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Atropine notes

2013-01-13T18:46:15Z

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<td valign="top" width="50%">Other Names

Atropin, atropina, atropinum, atropium, DL-hyoscyamine,

d,l-hyoscyaminum, DL-tropyltropate,

(±)-hyoscyamine, 3u( luH,5uH)-tropanyl-(RS)tropate,

tropintropate

Substance type: tropane alkaloid

Atropine was first isolated from the deadly nightshade

(Atropa belladonna) in 1820 by Rudolph

Brandes, who named the compound after the

genus. Atropine is found in many plants of the

Nightshade Family (including the genera Atropa,

Brugmansia, Datura, Hyoscyamus, Latua, Mandragora).

Atropine is chemically related to cocaine

(Willstaedter 1889). It also is closely related to

scopolamine and hyoscyamine. Hyoscyamine,

which is present in many living plants, quickly

racemizes into atropine when the raw drugs are

dried or stored.

A therapeutic dosage is usually considered to

be 1 mg. It is possible that 10 fig is lethal for

children and babies, but not for adults:

Relatively high doses (10 mg atropine sulfate

and above) have a stimulating effect on the

central nervous system, affecting especially

the cerebrum, diencephalon, and medulla

oblongata. The arousal is followed by an

anesthesia-like paralysis that can lead to coma

and a fatal respiratory paralysis. (Roth et al.

1994,945*)

The lethal oral dosage for an adult is approximately

100 mg (Roth et al. 1994, 765*).

The range of atropine's effects includes

psychomotor agitation, excitation, constant repetition

of a particular activity pattern, a need to

talk, euphoria, crying spells, confused speech,

hallucinations, spasms, delirium, flushing of the

skin, drying of the mucous membranes, coma,

unconsciousness, and heart arrhythmia (Roth et

al. 1994, 945*). One particularly characteristic

effect is a long-lasting dilation of the pupils (mydriasis).

It is because of this effect that atropine has

long been used in ophthalmology (Jurgens 1930).

Atropine is also utilized as a component in certain

anesthetics (in combination with morphine).

Injections of atropine are often administered prior

to surgery so that the mucous membranes will

remain dry during the procedure and the patient

will not choke on his or her own saliva. Atropine

has also been used to treat asthma (Terray 1909).

When it is given orally, the typical effects of atropine (dry mouth, pupillary dilation, increased

pulse rate) manifest about twice as strong as compared

to intramuscular injection (Mirakhur 1978).

Some of the atropine is excreted in the urine

unchanged (Roth et al. 1994,945*).

Atropine is an important antidote in cases of

poisoning (overdoses) caused by the fungal toxin

muscarine (cf. Inocybe spp.), Digitalis purpurea,

hydrogen cyanide, opium (cf. Papaver somniferum),

and morphine (Rompp 1995, 298*). Overdoses of

atropine can be successfully treated with morphine.

Because of its unpleasant side effects (dryness

of the mouth, difficulties in swallowing, disturbances

in vision, confusion), atropine as a pure

alkaloid has never acquired any cultural significance

as a psychoactive substance. However, the

medical literature does contain a few reports of

"atropine addiction" (Flincker 1932).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Atropine is available both as a pure substance and

as atropine sulfate. Although regulated as a

dangerous substance, it can be obtained with a

prescription and is not included on any list of

"narcotic drugs" (Koerner 1994, 1573*).

Literature

See also the entries for Atropa belladonna, Latua

pubiflora, cocaine, and tropane alkaloids.

Brandes, Rudolph. 1920. -aber das Atropium, ein

neues Alkaloid in den BHittern der Belladonna

(Atropa belladonna 1.). Journal fur Chemie und

Physik 28:9-31.

Flincker, R. 1932. -aber Abstinenz-Erscheinungen bei

Atropin. Munchner Medizinische Wochenschrift

17:540-41.

Jurgensen, E. 1930. Atropin im Wandel der Zeiten.

Artztliche Rundschau (Munich; 1930): 5-8.

Ketchum, J. S., F. R. Sidell, E. B. Crowell, G. K.

Aghajanian, andA. H. Hayes. 1973. Atropine,

scopolamine and ditran: Comparative

pharmacology and antagonists in man.

Psychopharmacology 28:121-45.

Mirakhur, R. K. 1978. Comparative study of the

effects of oral and i.m. atropine and hyoscine in

volunteers. British Journal ofAnaesthesia 50 (6):

591-98.

Terray, Paul von. 1909. -aber Asthma Bronchiale und

dessen Behandlung mit Atropin. Medizinische

Klinik 1 (5): 79-83.

Willstatter, R. 1898. Uber die Constitution der

Spaltungsprodukte von Atropin und Cocain.

Berichte der Deutschen Chemischen Gesellschaft

31:1534-53.</td>
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Cocaine

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<td valign="top" width="50%">Other Names

Benzoylecgoninmethylester, cocain, cocaIn, cocaina,

d-cocain, erythroxylin, kokain, methylbenzoylecgonine,

methylbenzylekgonin, (±)-methyl- [3J3benzoyloxy-

2a( 1aH,5aH)-tropancarboxylate], 0benzoyl-

[(- )-ekgonin] -methylester, 3-benzoyloxy8-

methyl-8-azabicyclo [3.2.1] octan-2-carboxylicacidmethylester,

3J3 -benzoyloxy-2J3 -tropancarboxylicacid-

methylester

Street Names

Autobahn, blow, C, candy, charlie, coca, coca pura

(Spanish, "pure coca»), coco, coke, cousin, donuts,

doppelter espresso, flake, koks, la blanca, lady

snow, la rubiecita, line, linie, mama coca, nasenpuder,

nose candy, peach, perica, puro (Spanish,

"pure»), schnee, schneewittchen, schniefe, schnupfschnee,

sniff, snow, snowwhite, strasse, strasschen,

Ziggy's stardust

Empirical formula: C17H21N04

Substance type: coca alkaloid

The cocaine molecule is structurally related to

tropine and other tropane alkaloids (Roth and

Fenner 1988, 311*). Today, cocaine is the most

consumed psychoactive plant constituent in the

world. Pure cocaine (as a base) is not water soluble

but can be dissolved in alcohol, chloroform,

turpentine oil, olive oil, or acetone. Cocaine salts

are water soluble.



History

In 1860, the German chemist Albert Niemann first

isolated cocaine from the leaves of the Peruvian

coca bush (Erythroxylum coca). The German

pharmacist Friedrich Gaedeke (1855) may have

represented the alkaloid before this. By around

1870, cocaine was being used as an agent of

pleasure, and it was employed at this time to treat

alcohol and morphine withdrawal as well as

melancholy. The ophthalmologist Karl Koller, a

friend of Sigmund Freud, introduced cocaine as a

local anesthetic for eye surgery in 1884. Hermann

Goring's use of cocaine was famous, and Adolf

Hitler, who also used other stimulants (cf. strychnine),

is thought to have consumed cocaine as well

(Phillips and Wynne 1980, 112).

Later, other substances derived from cocaine,

including eucaine, procaine (= Novocaine), tetracaine

(= Pantocaine) (1930), lidocaine (= Xylocaine)

(1944), mepivacaine (= Scandicaine) (1957),

prilocain (= Xylonest) (1960), bupivacaine (1963),

and etidocain (= Duranest) (1972), were also used

as local anesthetics (Busch and Rummel 1990;

Schneider 1993, 19*). Holocaine was also regarded

as a substitute.

The goal of chemists and pharmacologists to

carve out the effective core of the cocaine

molecule and retain the desirable and remove

the undesirable effects was achieved in an

exemplary manner with the synthesis of procaine

(1905). (Busch and Rummel 1990, 490)

In 1923, Willstadter and his coworkers worked

out the complete synthesis of cocaine. The precursors

are succindialdehyde, methylamine, and

mono-methyl-J3-keto-glutarate. However, this synthesis

has never achieved pharmaceutical importance.

Practically speaking, all of the cocaine used

in the pharmaceutical industry is derived from the

coca plant. In 1976,410 kg of cocaine were legally

extracted for this purpose (Taschner and Richtberg

1982,64).

Production and Use

An analysis of thirteen South American Erythroxylum

species found that cocaine is present only

in Erythroxylum coca and Erythroxylum novogranatense

(Holmstedt et al. 1977). Hair analysis of

Egyptian mummies has revealed the presence of

ecgonin, the first metabolite of cocaine, which indicates

that the ancient Egyptians either consumed

cocaine or an unknown African plant that metabolizes

to ecgonin (Balabanova et al. 1992*).

The coca plantations that are the source of

cocaine are known as cocales. Bolivian huanaco

leaves (Erythroxylum coca var. coca) are preferred for

cocaine production because they are the highest

yielding. With good chemicals and chemists, it is

possible to produce 1 kg of pure cocaine from 100

kg of coca leaves. In the early 1980s, some 100 tons

ofpure cocaine were exported from Colombia alone.

The entire process of cocaine production, as

well as the smuggling routes, the cartels, and everything

from the connections between politicians

and the cartels to the consumption of cocaine

even by politicians in the White House, has been

documented in countless reports on the radio and

television and in magazines and well-researched

books (Morales 1989). It is difficult to escape the

impression that the cocaine saga is one of the bestknown

stories of our times but one that is officially

ignored. Our leaders still act as though the

Mafia is using the white powder to corrupt and

dominate the world. In reality, the chief benefactors

of the billion-dollar business are the banks

and the countless politicians and law-enforcement

personnel involved in the trade (Sauloy and Le

Bonniec 1994).

The snuffing of crystallized cocaine appears to

have been discovered in North America at the

beginning of the twentieth century and spread

from there. Shortly after 1900, pure cocaine was

being ingested together with betel and lime in

India, Ceylon (Sri Lanka), and Java. The use of

cocaine as an athletic doping agent began in the

1940s (Fiihner 1943, 195*). Little has changed

since that time. Cocaine dealers still find some of

their best customers in the soccer stars of the

German first league and sports heroes in the

United States.

Basuko is dried cocaine base (an intermediate

step in the production of the pure alkaloid).

Sucito, or joints made of basuko, have been

smoked in Colombia since about 1930 (Siegel

1982b, 274). Cocaine is usually produced as a

hydrochloride but sometimes also as an oxalate or

hypochloride (HCL). Street cocaine is almost

exclusively cocaine HCL. Most of the illicit cocaine

available in Europe is only about 30% pure, as the

expensive pure drug is usually "cut:' The substances

that are most commonly used to "cut"

cocaine are:

• Inactive additives: milk sugar (lactose), grape

sugar (glucose), baking powder, talc (talcum),

borax, cornstarch, innositol, mannitol

• Active additives: speed (amphetamine, fenetyllin,

ritalin) and "freeze" (novocaine, benzocaine),

PCP ("angel dust"), methedrine,

pemoline, yohimbine, lidocaine, procaine,

tetracaine, caffeine, quinine, heroin (Taschner

and Richtberg 1982,65; Voigt 1982,84)

Dosage

A «line" of cocaine typically contains between 20

and 100 mg of cocaine, depending on the purity of

the substance and the consumer's preference.

Many users consume between 2 and 3 g in a day or

night. It is said that «the first line of the day is the

best."

Ritual Use

Cocaine has been called the champagne of drugs,

the drug of high society, the drug of the rich, et

cetera, and. it is certainly most often associated

with the wealthier classes. As a result, consumption

of the drug has taken on a strong social

character. Cocaine is rarely used by one person

alone. When it is taken with others, the consumption

follows a rather well-defined ritual. The person

providing the costly substance lays out several

lines (preferably on a mirror), then takes a

currency note (often of high value) and rolls it up.

One end of the rolled bill is placed in a nostril and

held with one hand, while the other hand is used

to press the other nostril closed. Half of one line,

or a small line, is then snuffed into the nostril. The

person then switches nostrils and snuffs the

remaining powder, after which the mirror is

passed to the next person. This circle may be

repeated several time, and it is customary for each

of several participants to prepare lines from their

own supply.

Artifacts

The cultural significance of cocaine in the modern

world cannot be overlooked. Artists, musicians,

and writers use it as a stimulant, while highly paid

computer experts, software engineers, and programmers

would hardly be able to keep up with

the demands of their jobs without their «coke."

Stockbrokers, financial gurus, and election staffers

may use cocaine until they are ready to collapse.

Even some of the soccer stars who jog into the

stadium sporting T-shirts with such incongruous

imprints as «Keine Macht den Drogen" C(No

Power to Drugs") are high as a kite on cocaine.

According to several estimates, the highest per

capita consumption of cocaine is found in Silicon

Valley and on Wall Street.

The first literary treatment of cocaine is found

in the Sherlock Holmes novel A Scandal in

Bohemia, by Sir Arthur Conan Doyle, published

only two years after Koller's discovery (Phillips

and Wynne 1980, 45). In this book, the astonishing

abilities of this brilliant detective are attributed in

part to his use of cocaine. By the time of the following

novel, The Sign of the Four, Sherlock

Holmes is injecting the pure alkaloid intravenously

(Voigt 1982,38).

The most famous novel of the British writer

Robert Louis Stevenson, Dr. Jekyll and Mr. Hyde,

was written in only four or six days and nightswith

the assistance of the magic powder, of course

(Springer 1989,8; Voigt 1982,38).

The novellas of the expressionist poet Walter

Rheiner (1895-1925), in which he referred to the

drug as «the eternal poison" and «the loved and

hated poison," played a great role in shaping the

image of demonic seduction by pharmaceutical

cocaine (Rheiner 1979).

At the beginning of the twentieth century, the

physician Gottfried Benn (1886-1956) wrote and

published numerous poems about cocaine (of

which he was very fond) that at the time were

deemed rather shocking (Benn 1982; vom Scheidt

1981, 401). Many other authors have also been

inspired by cocaine, including Georg Trakl,

Thomas Zweifel, Josef Maria Frank Fritz von

Ostini, Klaus Mann, and Jean Cocteau (Springer

1989).

Cocaine is also the subject of many novels. The

classic cocaine novel, Cocaine, was written by

Pitigrilli (= Dino Serge, 1927). The drug has often

been treated within its current criminal context

(Badekerl 1983; Fauser 1983), while other novels

have been written from a futuristic perspective (Boye 1986). The "coke scene" has also provided a

rich source of literary inspiration (McInerney

1984; Ellis 1986).

The composer Richard Strauss (1864-1949)

wrote his opera Arabella while under the influence

of cocaine (Springer 1989,8; Timmerberg 1996).494

Countless compositions have had cocaine as their

subject, including Cocaine IiI, for a mezzosoprano

and four female jazz singers, by the

contemporary composer Nancy van de Vate (CD

Ensemble Belcanto, Koch, 1994). From the 1920s

to the 1940s, the white powder fueled the work of

especially jazz and blues musicians, and Chick

Webb, Luke Jordan, and Dick Justice even gave it a

musical treatment ("Cocaine Blues").

Veritable blizzards of cocaine have passed

through the brains of many of rock music's greats,

who then set their experiences with the "fuel" to

music. A few examples are Country Joe McDonald

("Cocaine"), Black Sabbath ("Snowblind"), Little

Feat C'Sailin' Shoes"), the Rolling Stones ("Let It

Bleed"), Jackson Browne ("Cocaine"), and David

Bowie ("Ziggy Stardust").

The "hippie" band known as the Grateful Dead

sang about the white powder in their song

"Truckin'," one of their few hits to make it onto the

charts. Eric Clapton's interpretation of J. J. Cale's

song "Cocaine" became a worldwide success and

has been played millions of times over. The reggae

artist Dillinger released an album named Cocaine.

The drug also left its mark on the German music

scene, influencing or even appearing in the music

of Hannes Wader, Konstantin Wecker, Abi Ofarim,

and T'MA a.k.a. Falco ("Mutter, der Mann mit

dem Koks ist da" ["Mother, the Man with the Coke

Is Here"]; BMG Records 1995).

Cocaine has been the subject of at least one

theater work: The American playwright Pendleton

King wrote a piece entitled Cocaine that was

produced for the stage in 1917 (Phillips and

Wynne 1980,93 ff.).

Medicinal Use

The medicinal applications of cocaine were

discovered only a short time after the isolation of

the molecule itself. Cocaine was initially used for

local anesthesia495 in ophthalmology and dentistry,

and infiltration anesthesia was developed just

a few years later (Custer 1898). Because analogs

(e.g., procaine) were developed that produce

specific effects with no psychoactive side effects,

cocaine is rarely used as an anesthetic today.</td>
<td valign="top" width="53%">Pharmacology and Effects

Cocaine stimulates the central nervous system,

especially the autonomic (sympathetic) system,

where it inhibits the reuptake of the neurotransmitters

noradrenaline, dopamine, and

serotonin and increases the time in which they

remain in the synaptic cleft. Cocaine has a powerful effect upon the peripheral nervous

system, which explains its efficaciousness as a local

anesthetic. It has strong stimulant and vasoconstricting

properties. Very high dosages of cocaine

are said to be able to induce hallucinations, an

effect that is frequently noted in the neurological

literature (Pulvirenti and Koob 1996,49) as well as

in prose and poetry (Rheiner 1979, 27).

Hallucinations (of nonexistent people, images,

flickering lights) often occur during nights in

which dosages of 2 to 3 g have been taken. For

many people, cocaine also dispels fear. It stimu1ates

a need for alcoholic beverages at the same

time that it strongly suppresses the effects of

alcohol. A similar dynamic applies to nicotine.

In a certain sense, there is something unsatisfying

about the effects of cocaine. A person may

sense that satisfaction could be achieved if the

effects could possibly be increased. However, using

more cocaine does not produce an enhancement

of its effects.

Just as coca was and is employed in South

America as an aphrodisiac, cocaine has a similar

use in the West. Cocaine's reputation as an aphrodisiac

can be traced back to Sigmund Freud (1884)

and has been repeatedly confirmed in the

pharmacological literature:

At a high level of intoxication, central

excitation sets in with characteristic shivering,

an initial state of euphoria that turns into

delirium and hallucinations. For women, the

stimulation ... not infrequently has an erotic

character and has resulted in later accusations

of sexual misconduct against the operating

physician. (Fiihner 1943, 196*)

Some psychiatrists believe that cocaine stimulates

the "sexual center" of the brain (Siegel

1982a). For many users, cocaine is inevitably

associated with sexuality (MacDonald et al. 1988;

Phillips and Wynne 1980,221).

Cocaine relaxes and opens the sphincter

muscles, which makes anal penetration easier as

well as substantially more pleasurable. However,

cocaine (much like ephedrine) often has an

adverse effect on erectile function and consequently

leads to temporary impotence (cf. Siegel

1982a).

The addictive potential of cocaine has been the

subject of much debate. This issue does not appear

to be oriented toward the user as much as it

reflects the current legal situation. In recent years,

there have been efforts to develop a vaccination

against "cocaine addiction." Of course, the

research in this area is conducted on rats (Hellwig

1996). The effect of cocaine on the brain is also an

object of much research, since studies that

confirm the adverse effects of cocaine are likely to

receive financial support from the government. Studies that do not have a political agenda are the

exception rather than the rule (Volkow and Swann

1990).

People who use cocaine frequently suffer from

a runny nose ("coke sniffles") the following day.

Users may counteract this undesirable and

unpleasant aftereffect by rinsing their nose with a

saline solution (e.g., with medicinal salts). Many

users rub vitamin E oil in their nose, a practice

said to regenerate the highly irritated mucous

membranes in the nose (Voigt 1982,72). Although

cocaine can be very helpful in dealing with an

acute attack of hay fever, chronic use can actually

contribute to the condition.

Crack or Free-Base Cocaine

In the German press, crack has been portrayed as

"death for a few dollars," "the devil's drug from the

U.S.A.;' et cetera. The general idea seems to be that

"cocaine was a miracle, but crack, crack was better

than sex" or "cocaine was purgatory-but crack is

hell" (in Wiener 6 [1986]: 65,66).

Crack, which is also known as base, free base,

baseball, rocks, Roxanne, and supercoke, is

nothing more than smokeable free-base cocaine

(Siegel 1982b). In other words, crack is cocaine in

the form of a free base (Pulvirenti and Koob 1996,

48). It can be obtained from an aqueous solution

of cocaine hydrochloride to which an alkaline

substance (such as sodium carbonate) is added.

The cocaine salt is transformed into the pure base,

or, in other words, the pure substance. It can then

be purified with ether, causing the cocaine to

crystallize out. Crack is usually "smoked" (i.e.,

vaporized and inhaled) in glass pipes. A typical

dosage ranges from 0.05 to 0.1 g. The effect is very

similar to that of snuffed cocaine but is much

more intense:

Although crack is a derivative of cocaine, there

is little comparison between the mild and

mostly stimulating cocaine inebriation and

the effects of the short-term crack high, which

can literally bowl one over. Whereas cocaine

produces a euphoric sensation of great concentration

and razor-sharp intelligence for

about 20 to 60 minutes, crack lasts for only

three to five minutes while giving the consumer

an incredibly strong kick with regard to

physical sensations as well as the euphoria of

absolute omnipotence. Of course, this has

resulted in many myths, including one that

crack is particularly pure. (Sahihi 1995,37*)

Ethnologists have begun using the field

methods typical of the discipline to study the

"crack phenomenon;' which appears to be a

typically American product (Holden 1989).

"Crack life" is a reflection of the problems in

American society and reveals deep social fissures and cultural anomalies. For users, the "crack way"

is an important form of identity formation. Crack

is frequently found together with prostitution, as

"addicts" may accept it as a form of payment for

sexual services (Carlson and Siegal 1991).

On the street, the following substances may be

used as substitutes for cocaine or crack in times of

shortage: procaine, caffeine, benzocaine, phenylpropanolamine,

lidocaine, and ephedrine (Siegel

1980).

Commercial Forms and Regulations

Cocaine hydrochloride is available through the

pharmacy trade. The German Drug Law lists

cocaine as a "narcotic drug in which trafficking is

allowed but which may not be prescribed"

(Korner 1994, 42). In the United States, the Controlled

Substances Act classifies cocaine as a

Schedule II substance.

Literature

See also the entries for Erythroxylum coca,

Erythroxylum novogranatense, atropine, and

tropane alkaloids.

Ashley, Richard. 1975. Cocaine: Its history, use and

effects. New York: St. Martin's Press.

Aurep, B. von. 1880. Dber die physiologische

Wirkung des CocaYn. Archiv fur Physiologie

21:38-77.

Badekerl, Klaus. 1983. Ein Kilo Schnee von Gestern.

Munich and Zurich: Piper.

Benn, Gottfried. 1982. Gedichte, in der Fassung der

Erstdrucke. Frankfurt/M.: Fischer.

Boye, Karin. 1986. Kallocain: Roman aus dem 21.

Jahrhundert. Kiel: Neuer Malik Verlag.

Biisch, H. P., and W. Rummel. 1990.

Lokalanasthetika, Lokalanasthesie. In Allgemeine

und spezielle Pharmakologie und Toxikologie (5th

ed.), ed. W. Forth, D. Heuschler, and W. Rummel,

490-96. Mannheim, Vienna, and Zurich: B. 1.

Wissenschaftsverlag.

Carlson, Robert G., and Harvey A. Siegal. 1991. The

crack life: An ethnographic overview of crack use

and sexual behavior among African-Americans

in a Midwest metropolitan city. Journal of

Psychoactive Drugs 23 (1): 11-20.

Crowley, Aleister. 1973. Cocaine. San Francisco:

And/Or Press.

Custer, Julius, Jr. 1898. Cocain und

Infiltrationanasthesie. Basel: Benno Schwabe.

Ellis, Bret Easton. 1987. Less Than Zero. New York:

Random House.

Fauser, Jorg. 1983. Der Schneemann. Reinbek:

Rowohlt.

Fischer 5., A. Raskin, and E. Uhlenhuth, eds. 1987.

Cocaine: Clinical and biobehavioral aspects. New

York: Oxford University Press.

Freud, Sigmund. 1884. Uher Coca. Centralblatt fur

die gesamte Therapie 2:289-314. Repr. in

Taschner and Richtberg 1982,206-31 (see

below).

---. 1885. Dber die Allgemeinwirkung des

Cocains. Medizinisch-chirurgisches Centralblatt

20:374-75.

---.1887. Bemerkungen tiber Cocainsucht und

Cocainfurcht, mit Beziehung auf einen Vortrag

von W. A. Hammonds. Wiener medizinische

Wochenschrift 37:927-32.

---.1996. Schriften uber Kokain. Frankfurt/M.:

Fischer. (Orig. pub. 1884.)

Gay, George R. 1981. You've corne a long way, baby!

Coke time for the new American lady of the

eighties. Journal ofPsychoactive Drugs 13 (4):

297-318.

Gottlieb, Adam. 1979. The pleasures ofcocaine. San

Francisco: And/Or Press.

Grinspoon, Lester, and James B. Bakalar. 1985.

Cocaine: A drug and its social evolution. Rev. ed.

New York: Basic Books.

Hartmann, Walter. 1990. Informationsreihe Drogen:

Kokain. Markt Erlbach: Raymond Martin Verlag.

Hellwig, Bettina. 1996. Impfung gegen Cocain?

Deutsche Apotheker-Zeitung 136 (4): 46/270.

Holden, Constance. 1989. Streetwise crack research.

Science 246:1376-81.

Holmstedt, Bo, Eva Jaatmaa, Kurt Leander, and

Timothy Plowman. 1977. Determination

of cocaine in some South American species of

Erythroxylum using mass fragmentography.

Phytochemistry 16:1753-55.

Kennedy, J. 1985. Coca exotics: The illustrated story of

cocaine. New York: Cornwall Books.

Koller, Carl [= Karl]. 1884. Dber die Verwendung des

CocaYn zur Anasthetisierung am Auge. Wiener

medizinische Wochenschrift 34: 1276-1278,

1309-1l.

---. 1935. Nachtragliche Bemerkungen tiber die

ersten Anfange der Lokalanasthesie. Wiener

medizinische Wochenschrift 85:7.

---. 1941. History of cocaine as a local

anesthetic. Journal ofthe American Medical

Association 117: 1284.

Lindgren, J.-E. 1981. Guide to the analysis of cocaine

and its metabolites in biological material. Journal

ofEthnopharmacology 3:337-5l.

Lossen, W. 1865. Dber das Cocain. Liebig's Annalen

133:351-71.

MacDonald, P. T., V. Waldorf, C. Reinarman, and

S. Murphy. 1988. Heavy cocaine use and sexual

behavior. Journal ofDrug Issues 18 (3): 437-55.

Maier, Hans Wolfgang. 1926. Der Kokainismus.

Leipzig: Thieme.

Mcinerney, Jay. 1984. Bright Lights, Big City. New

York: Knopf.

Morales, Edmundo. 1989. Cocaine: White gold rush in

Peru. Tucson and London: The University of

Arizona Press.

Niemann, Albert. 1860. Dber eine neue organische

Base in den Cocablattern. Dissertation,

Gottingen University.

Pernice, Ludwig. 1890. Dber Cocainanaesthesie.

Deutsche medizinische Wochenschrift 16:287.

Phillips, Joel 1., and Ronald D. Wynne. 1980.

Cocaine: The mystique and the reality. New York:

Avon Books.

Plasket, B., and E. Quillen. 1985. The white stuff. New

York: Dell Publishing Co.

Pulvirenti, Luigi, and George F. Koob. 1996. Die

Neurobiologie der Kokainabhangigkeit. Spektrum

der Wissenschaft 2:48-55. (An unethical and

nauseating study on animals.)

Rheiner, Walter. 1979. Kokain: Eine Novelle und

andere Prosa. Berlin and Darmstadt: Agora

Verlag. Repr. 2nd ed., 1982.

Richards, Eugene. 1994. Cocaine true, cocaine blue.

New York: Aperture.

Roles, R., M. Goldberg, and R. G. Sharrar. 1990. Risk

factors for syphilis: Cocaine use and prostitution.

American Journal ofPublic Health 80 (7): 853-57.

Sabbag, Robert. 1976. Snowblind: A briefcareer in the

cocaine trade. Indianapolis and New York: The

Bobbs-Merrill Co.

Sauloy, Mylene, and Yves Le Bonniec. 1994.

Tropenschnee-Kokain: Die Kartelle, ihre Banken,

ihre Gewinne. Ein Wirtschaftsreport. Reinbek bei

Hamburg: Rowohlt.

Siegel, Ronald K. 1978. Cocaine hallucinations.

American Journal ofPsychiatry 135:309-14.

---.1980. Cocaine substitutes. New England

Journal ofMedicine 302:817-18.

---. 1982a. Cocaine and sexual dysfunction: The

curse of Mama Coca. Journal ofPsychoactive

Drugs 14 (1-2): 71-74.

---. 1982b. Cocaine smoking. Journal of

Psychoactive Drugs 14 (4): 271-359.

Smith, David E., and Donald R. Wesson. 1978.

Cocaine. Journal ofPsychedelic Drugs 10 (4):

351-60.

Springer, Alfred, ed. 1989. Kokain: Mythos und

Realitiit-Eine kritisch dokumentierte Anthologie.

Vienna and Munich: Verlag Christian

Brandstatter.

Taschner, Karl-Ludwig, and Werner Richtberg. 1982.

Kokain-Report. Wiesbaden: Akademische

Verlagsgesellschaft.

Thamm, Berndt Georg. 1985. Das Kartell: Von

Drogen und Miirkten-ein modernes Miirchen.

Basel: Sphinx.

---. 1986. Andenschnee: Die lange Linie des

Kokain. Basel: Sphinx.

Timmerberg, Helge. 1996. Kaltmacher Kokain.

Tempo 3:34-42.

Turner, Canton E., Beverly S. Urbanek, G. Michael

Wall, and Coy W. Waller. 1988. Cocaine: An

annotated bibliography. 2 vols. Jackson and

London: Research Institute of Pharmaceutical

Sciences/University Press of Mississippi.

Voigt, Hermann P. 1982. Zum Thema: Kokain. Basel:

Sphinx.

Volkow, Nora v., and Alan C. Swann, eds. 1990.

Cocaine in the brain. New Brunswick, N.J.:

Rutgers University Press. (See book review by

Ronald Siegel in Journal ofPsychoactive Drugs 23

(1; 1991): 93 f.)

vom Scheidt, Jurgen. 1973. Freud und das Kokain.

Psyche (Munich) 27:385-430.

---.1981. Kokain. In Rausch und Realitat, ed. G.

Volger, 1:398-402. Cologne: Rautenstrauch-Joest

Museum fur Volkerkunde.

Wesson, Donald R. 1982. Cocaine use by masseuses.

Journal ofPsychoactive Drugs 14 (1-2): 75-76.

Wolfer, P. 1922. Das Cocain, seine Bedeutung und

seine Geschichte. Schweizerische medizinische

Wochenschrift 3:674-79.</td>
</tr>

</table>

Bufotenine

2013-01-13T18:44:32Z

205.56.181.196:

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Bufotenin, 5-hydroxy-N,N-dimethyltryptamine,

5-0H-DMT, mappin, N,N-dimethylserotonin, 3[

2-(dimethylamino)ethyl] -IH-indol-5-01

Substance type: tryptamine (indole alkaloid)

Bufotenine was first isolated in 1893 from secretions

of the common toad (Bufo vulgaris 1.)

(Shulgin 1981). In 1954, it was found in Anadenanthera

peregrina. Bufotenine also occurs in the

false death cap (Amanita citrina [Schaeff.] S.P.

Gray) (Keup 1995, 11; Wieland and Motzell953)

and in other members of the genus (cf. Amanita

pantherina). Indeed, the symbolic relationship

between toads and mushrooms is very interesting

in this context (see Amanita muscaria). Bufotenine

has also been found in Anandenanthera

colubrina (Piptadenia spp.), Arundo donax, Banisteriopsis

spp., Mucuna pruriens, and Phragmites

australis. Bufotenine is a tryptamine derivative

and is closely related to N,N-DMT, 5-MeO-DMT,

and psilocybin and psilocin. Chemically, it is

almost identical to melatonin (for more on

melatonin, see Reiter and Robinson 1996).

Bufotenine has been detected in human urine

on numerous occasions (Raisanen 1985) and thus

we know that it is a natural substance that is

metabolized in the human body. The molecule is

very stable. Approximately 16 mg is considered to

be an effective dosage. The pharmacology of the

substance has been little studied.

The first report of the hallucinogenic effects of

bufotenine was published by Fabing and Hawkins

(1956), who tested the substance on prison

inmates (probably against their will). This was

followed by additional research with humans,

including some studies in which the substance was

tested under highly unethical conditions by being

injected into patients in a closed psychiatric

institution without their permission, or even

against their will. The patients were administered

overly high doses and also subjected to

electroshocks and other procedures. In this

setting, no visions were reported. It was concluded

that bufotenine does not produce visions but has

only toxic effects (Turner and Merlin 1959).

Subsequent studies strengthened the theory that

bufotenine should not be classified as a

hallucinogen (Mandell and Morgan 1971). A more

recent study using only one subject found no

hallucinogenic effects, although changes in the

emotional domain were observed (McLeod and Sitram 185). Almost all of the reports have noted

that the faces of the test subjects turned red or

even purple (Fabing and Hawkins 1956). The

belief that bufotenine is not a true psychedelic

drug has persisted into the present day (e.g., Lyttle

et al. 1996; this study, however, is not based on any

personal experiments). In its pure form,

bufotenine has never acquired any cultural

significance as a psychoactive substance.

Bufotenine and Bufo marinus

Since ancient times, there have been numerous

reports of toads being used to prepare love drinks

and other witches' brews, and even witches'

ointments (Degraaff 1991; Hirschberg 1988).

Researchers (prematurely) dismissed such reports

as fantasy. In China and Mesoamerica, there is

good evidence for the use of toads in magical

brews. Chinese toad secretions (ch'an su) contain

large amounts of bufotenine (Chen and Jensen

1929). In China and Japan, preparations containing

bufotenine are sold as aphrodisiacs (Lewis 1989,

70).491

In Mesoamerica, the toad was regarded as a

manifestation of the Earth Mother, for example, in

the form of the Aztec earth goddess Tlatecuhtli

(Furst 1972; 1974, 88*). In the region, toads (and

frogs) are associated with the rain gods (chac) and

rainmaking. The Tarahumara refer to toads as

"powerful rainmakers." The Olmecs-whose culture

is thought to have been the first Mesoamerican

civilization-depicted toads in their

sacred art and probably used them as hallucinogens.

An Olmec object made of green jade and

shaped like a toad has been interpreted as a tray

for snuff powder (Peterson 1990,46*). In general,

the toad was probably the most important Olmec

deity (Furst 1981; Furst 1996*; Kennedy 1982;

Taylor n.d.).

A cylindrical ceramic container (late Classic

period) containing a Bufo marinus (cane toad)

skeleton was found in Seibal, a Mayan ceremonial center. It may have been used as a vessel for

drinking balche'. Hundreds of ritually interred

cane toad skeletons were discovered in postClassic

Mayan ritual depots on the Caribbean

island of Cozumel (Hamblin 1981; 1984,53 ff.). A

report from the colonial period indicates that

toads were an ingredient in balche' or chicha. Bufo

marinus is also an ingredient in zombie poison.

In Mesoamerica, Bufo marinus is known

variously as henhen (Tzeltal; cf. Hunn 1977, 247),

bab (Mayan), ah bab (Lacandon), and tamazolin

(Aztec). Numerous stone sculptures of toads as

well as some toad bones were discovered in the

main temple (Templo Mayor) of the Aztecs

(Ofrenda 23; Alvarez and Ocana 1991, 117, 128).

All of the finds suggest that Bufo marinus was used

in rituals or had a cosmological significance.

Today, some Mexican Indians still eat skinned

toads, while their secretions are sold at Mexican

brujeria markets as a love powder. The toad itself is

invoked as a love magic in magical prayers

(oraci6n del sapo). The toad's mucus is rolled into

little balls that are then rubbed behind the ear as

an aphrodisiac. Many people in Mexico still wear

toad-shaped amulets today; they may, for

example, be made from amber or obsidian from

Chiapas.

In the southern part of Veracruz, curanderos

("healers") or brujos ("sorcerers") still use a preparation

of Bufo marinus. To prepare it, they capture

and kill ten toads. The glands are removed and

crushed to produce a paste, to which lime (probably

slaked lime) and ashes from a botanically

unidentified plant called tamtwili are added. The

combination is then mixed in water and boiled

until· there is no more "bad smell" (usually all

night long). The solution is then mixed with

chicha (maize beer) and filtered. The remaining

fluid is kneaded into maize dough, lime brine, and

five kernels of sprouted maize, and the mixture is

laid out in the sun for a few days so that it can

ferment, after which it is dried over a fire. This

product (piedrecita, "little rocks") is then stored

far away from any human dwellings. In earlier

times, special huts were used to store this magical

substance. For consumption, a few pieces are cut

off, ground, and soaked in water. After the

insoluble ingredients have settled, the solution is

poured off and boiled for a considerable time until

it gives off a certain odor. Today, the drink is no

longer ingested collectively but is used by only one

person at a time under the supervision of a

curandero. The effects begin after approximately

thirty minutes and are first manifested as an

increase in the pulse rate and a shaking of the

muscles and limbs, followed by headaches and

delirium. This state lasts three to five hours. In

former times, the drinking of this brew was an

important part of the initiation of boys into

adulthood. Sacred songs were sung to the initiate while he was delirious. The initiate was told to

allow the visions he was going to experience to

impress themselves well upon him (Knab n.d.).

It appears that the hallucinogenic effects of

Bufo marinus were also known in Argentina, for it

is considered there to be one of the "temptations"

of Saint Anthony (see Claviceps purpurea)

(Rosemberg 1951).

Originally from the Americas, Bufo marinus

was .introduced to Australia, where it is now

known as the cane toad and its secretions are

allegedly used as a psychoactive drug. Under

Queensland's Drug Misuse Act, bufotenine is an

illegal substance in Australia (Ingram 1988,66). In

recent years, the press has been reporting

increasing cases of toad lickin' (Lyttle 1993), a

practice in which the secretions of Bufo marinus

are licked off the toad:

When licking the expressed secretions (abusers

reported that it is possible to "milk" twice a

day), a furry sensation on the lips and tongue

quickly becomes manifest. Five to ten (up to

30) minutes later, nausea is common, and only

20 to 30 minutes after ingestion, sometimes

earlier, hallucinations of various kinds set in,

beginning more rapidly and not lasting as

long as with LSD. (Keup 1995, 12)

The thickened juice of boiled animals is also

ingested in Australia (Keup 1995, 14). A decoction

of the dried skin (known as cane skin tea) is also

used (DerSpiegel32 [1994]: 92).

The secretions from Bufo marinus contain

catecholamines (dopamine, N-methyldopamine,

adrenaline, noradrenaline) and tryptamines (serotonin,

N-methyl-serotonin, bufotenine, bufotenidine,

dehydrobufotenine), as well as glycoside-like

toad toxins (Deulofeu and Ruveda 1971; Lyttle

1993, 523 f.). The skin has been found to contain

morphine. The toad toxins (bufotoxine, bufogenine,

and bufadienolides) are cardiotoxic and

are similar to digitalis in their effects: nausea,

vomiting, increase in blood pressure, confusion,

and psychotic states (Keup 1995, 12). Smoking is

probably the safest method to ingest Bufo marinus

secretions, as the burning process apparently

destroys the toxic components while leaving the

bufotenine intact (Alexander Shulgin, pers.

comm.). The ethnobotanist Brett Blosser smoked

dried Bufo marinus secretions (approximately 1

mg every few minutes) and reported experiencing

tryptamine-like hallucinations similar to those

induced by the secretions of Bufo alvarius (cf.

5-MeO-DMT) (B. Blosser, pers. comm.).

The few reports of the effects of smoked toad

skin indicate that they are hallucinogenic. One

Australian user stated, "I am seeing the world

through the consciousness of a toad" (Lewis 1989,

71).

The following species of toads contain significant

amounts of bufotenine: Bufo alvarius (cf. 5MeO-

DMT), B. americanus, B. arenarum, B. bufo

bufo, B. calamita, B. chilensis, B. crucifer, B. formosus,

B. fowleri, B. paracnemis, B. viridis (Deulofeu

and Ruveda 1971, 483).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Bufotenine is marketed as bufotenine hydrogen

oxalate. In the United States, bufotenine is classified

as a Schedule I drug (Shulgin 1981). In contrast,

in Germany it is not considered a narcotic

and is not illegal (Korner 1994, 1572*).

Literature

See also the entries for Anandenanthera colubrina

and 5-MeO-DMT.

Allen, E. R., and W. T. Neill. 1956. Effects of marine

toad toxins on man. Herpetologica 12:150-5l.

Alvarez, Ticul, and Aurelio Ocana. 1991. Restos oseos

de vertebrados terrestres de las ofrendas del

Templo Mayor, ciudad de Mexico. In La fauna en

el Templo Mayor, ed. B. Quintanar, 105-46.

Mexico City: INAH.

Chen, K. K., and H. Jensen. 1929. A pharmacognostic

study of ch'an su, the dried venom of the Chinese

toad. Journal ofthe American Pharmaceutical

Association 23:244-5l.

Davis, Wade. 1988. Bufo marinus: New perspectives

on an old enigma. Revista de la Academia

Columbiana de las Ciencies Exactas, Fisicas y

Naturales 14 (63): 151-56.

Degraaff, Robert M. 1991. The book ofthe toad.

Rochester, Vt.: Park Street Press.

Deulofeu, Venancio, and Edmundo A. Ruveda. 1971.

The basic constituents of toad venoms. In

Venomous animals and their venoms, ed.

Wolfgang Bucherl and Eleanor E. Buckley,

475-556. New York and London: Academic Press.

Fabing, Howard D., and J. Robert Hawkins. 1956.

Intravenous bufotenine injection in the human

being. Science 123:886-87.

Furst, Peter T. 1972. Symbolism and

psychopharmacology: The toad as earth mother

in Indian America. In Religion en Mesoamerica,

XII Mesa Redondo, 37-46. Mexico City: S.M.A.

---. 1981. Jaguar baby or toad mother: A new

look at an old problem in Olmec iconography. In

The Olmec and their neighbors, ed. E. Benson,

149-62. Washington, D.C.: Dumbarton Oaks.

Hamblin, Nancy 1. 1981. The magic toads of

Cozumel. Mexicon 3 (I): 10-13.

---. 1984. Animal use by the Cozumel Maya.

Tucson: The University of Arizona Press.

Hirschberg, Walter. 1988. Frosch und KrOte in Mythos

und Brauch. Vienna: Bohlau.

Hunn, Eugene S. 1977. Tzeltal folk zoology. New York:

Academic Press.

Ingram, Glen. 1988. The ''Australian'' cane toad. In

Venoms and victims, ed. John Pearn and Jeanette

Covacevich, 59-66. Brisbane: The Queensland

Museum and Amphion Press.

Kennedy, Alison B. 1982. Ecce Bufo: The toad in

nature and Olmec iconography. Current

Anthropology 23 (2): 273-90.

Keup, Wolfram 1995. Die Aga-Krote und ihr Sekret:

Inhaltsstoffe und MiBbrauch. Pharmazeutische

Zeitung 140 (42): 9-14.

Knab, Tim. n.d. Narcotic use of toad toxins in

southern Veracruz. Unpublished manuscript.

(Ten typewritten pages.)

Lewis, Stephanie. 1989. Cane toads: An unnatural

history. New York: Dolphin/Doubleday.

Lyttle, Thomas. 1993. Misuse and legend in the "toad

licking" phenomenon. The International Journal

ofthe Addictions 28 (6): 521-38.

Lyttle, Thomas, David Goldstein, and Jochen Gartz.

1996. Bufo toads and bufotenine: Fact and fiction

surrounding an alleged psychedelic. Journal of

Psychoactive Drugs 28 (3): 267-90. (Contains an

excellent bibliography.)

Mandell, A. J., and M. Morgan. 1971.

Indole(ethyl)amine N-methyltransferase in

human brain. Nature 230:85-87.

McLeod, W. R, and B. R Sitram. 1985. Bufotenine

reconsidered. Psychiatria Scandinavia 72:447-50.

Raisanen, Martti. 1985. Studies on the synthesis and

excretion of bufotenine and N,Ndimethyltryptamine

in man. Academic

dissertation, Helsinki, University of Helsinki.

Reiter, Russel J., and Jo Robinson. 1996. Melatonin.

Munich: Droemer Knaur.

Rosenberg, Tobias. 1951. El sapo en el folklore y en la

medicina. Buenos Aires: Editorial Periplo.

Shulgin, Alexander T. 1981. Bufotenine. Journal of

Psychoactive Drugs 13 (4): 389.

Taylor, Michael. 1993. The use of the Bufo marinus

toad in ancient Mesoamerica. Crash Collusion 4:

53-55.

Turner, W. J., and S. Merlis. 1959. Effects of some

indolalkylamines on man. Archives ofNeurology

and Psychiatry 81:121-29.

Verpoorte, R., Phan-Quoc-Kinh, and A. Baerheim

Svendsen. 1979. Chemical constituents of

Vietnamese toad venom collected from Bufo

melanostictus Schneider. Journal of

Ethnopharmacology 1:197-202.

Wieland, Theodor, and Werner Motzel. 1953. Dber

das Vorkommen von Bufotenin im gelben

Knollenblatterpilz. Justus Liebigs Annalen der

Chemie 581:10-16.</td>
</tr>

Bufotenine

2013-01-13T18:44:00Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Bufotenin, 5-hydroxy-N,N-dimethyltryptamine,

5-0H-DMT, mappin, N,N-dimethylserotonin, 3[

2-(dimethylamino)ethyl] -IH-indol-5-01

Substance type: tryptamine (indole alkaloid)

Bufotenine was first isolated in 1893 from secretions

of the common toad (Bufo vulgaris 1.)

(Shulgin 1981). In 1954, it was found in Anadenanthera

peregrina. Bufotenine also occurs in the

false death cap (Amanita citrina [Schaeff.] S.P.

Gray) (Keup 1995, 11; Wieland and Motzell953)

and in other members of the genus (cf. Amanita

pantherina). Indeed, the symbolic relationship

between toads and mushrooms is very interesting

in this context (see Amanita muscaria). Bufotenine

has also been found in Anandenanthera

colubrina (Piptadenia spp.), Arundo donax, Banisteriopsis

spp., Mucuna pruriens, and Phragmites

australis. Bufotenine is a tryptamine derivative

and is closely related to N,N-DMT, 5-MeO-DMT,

and psilocybin and psilocin. Chemically, it is

almost identical to melatonin (for more on

melatonin, see Reiter and Robinson 1996).

Bufotenine has been detected in human urine

on numerous occasions (Raisanen 1985) and thus

we know that it is a natural substance that is

metabolized in the human body. The molecule is

very stable. Approximately 16 mg is considered to

be an effective dosage. The pharmacology of the

substance has been little studied.

The first report of the hallucinogenic effects of

bufotenine was published by Fabing and Hawkins

(1956), who tested the substance on prison

inmates (probably against their will). This was

followed by additional research with humans,

including some studies in which the substance was

tested under highly unethical conditions by being

injected into patients in a closed psychiatric

institution without their permission, or even

against their will. The patients were administered

overly high doses and also subjected to

electroshocks and other procedures. In this

setting, no visions were reported. It was concluded

that bufotenine does not produce visions but has

only toxic effects (Turner and Merlin 1959).

Subsequent studies strengthened the theory that

bufotenine should not be classified as a

hallucinogen (Mandell and Morgan 1971). A more

recent study using only one subject found no

hallucinogenic effects, although changes in the

emotional domain were observed (McLeod and Sitram 185). Almost all of the reports have noted

that the faces of the test subjects turned red or

even purple (Fabing and Hawkins 1956). The

belief that bufotenine is not a true psychedelic

drug has persisted into the present day (e.g., Lyttle

et al. 1996; this study, however, is not based on any

personal experiments). In its pure form,

bufotenine has never acquired any cultural

significance as a psychoactive substance.

Bufotenine and Bufo marinus

Since ancient times, there have been numerous

reports of toads being used to prepare love drinks

and other witches' brews, and even witches'

ointments (Degraaff 1991; Hirschberg 1988).

Researchers (prematurely) dismissed such reports

as fantasy. In China and Mesoamerica, there is

good evidence for the use of toads in magical

brews. Chinese toad secretions (ch'an su) contain

large amounts of bufotenine (Chen and Jensen

1929). In China and Japan, preparations containing

bufotenine are sold as aphrodisiacs (Lewis 1989,

70).491

In Mesoamerica, the toad was regarded as a

manifestation of the Earth Mother, for example, in

the form of the Aztec earth goddess Tlatecuhtli

(Furst 1972; 1974, 88*). In the region, toads (and

frogs) are associated with the rain gods (chac) and

rainmaking. The Tarahumara refer to toads as

"powerful rainmakers." The Olmecs-whose culture

is thought to have been the first Mesoamerican

civilization-depicted toads in their

sacred art and probably used them as hallucinogens.

An Olmec object made of green jade and

shaped like a toad has been interpreted as a tray

for snuff powder (Peterson 1990,46*). In general,

the toad was probably the most important Olmec

deity (Furst 1981; Furst 1996*; Kennedy 1982;

Taylor n.d.).

A cylindrical ceramic container (late Classic

period) containing a Bufo marinus (cane toad)

skeleton was found in Seibal, a Mayan ceremonial center. It may have been used as a vessel for

drinking balche'. Hundreds of ritually interred

cane toad skeletons were discovered in postClassic

Mayan ritual depots on the Caribbean

island of Cozumel (Hamblin 1981; 1984,53 ff.). A

report from the colonial period indicates that

toads were an ingredient in balche' or chicha. Bufo

marinus is also an ingredient in zombie poison.

In Mesoamerica, Bufo marinus is known

variously as henhen (Tzeltal; cf. Hunn 1977, 247),

bab (Mayan), ah bab (Lacandon), and tamazolin

(Aztec). Numerous stone sculptures of toads as

well as some toad bones were discovered in the

main temple (Templo Mayor) of the Aztecs

(Ofrenda 23; Alvarez and Ocana 1991, 117, 128).

All of the finds suggest that Bufo marinus was used

in rituals or had a cosmological significance.

Today, some Mexican Indians still eat skinned

toads, while their secretions are sold at Mexican

brujeria markets as a love powder. The toad itself is

invoked as a love magic in magical prayers

(oraci6n del sapo). The toad's mucus is rolled into

little balls that are then rubbed behind the ear as

an aphrodisiac. Many people in Mexico still wear

toad-shaped amulets today; they may, for

example, be made from amber or obsidian from

Chiapas.

In the southern part of Veracruz, curanderos

("healers") or brujos ("sorcerers") still use a preparation

of Bufo marinus. To prepare it, they capture

and kill ten toads. The glands are removed and

crushed to produce a paste, to which lime (probably

slaked lime) and ashes from a botanically

unidentified plant called tamtwili are added. The

combination is then mixed in water and boiled

until· there is no more "bad smell" (usually all

night long). The solution is then mixed with

chicha (maize beer) and filtered. The remaining

fluid is kneaded into maize dough, lime brine, and

five kernels of sprouted maize, and the mixture is

laid out in the sun for a few days so that it can

ferment, after which it is dried over a fire. This

product (piedrecita, "little rocks") is then stored

far away from any human dwellings. In earlier

times, special huts were used to store this magical

substance. For consumption, a few pieces are cut

off, ground, and soaked in water. After the

insoluble ingredients have settled, the solution is

poured off and boiled for a considerable time until

it gives off a certain odor. Today, the drink is no

longer ingested collectively but is used by only one

person at a time under the supervision of a

curandero. The effects begin after approximately

thirty minutes and are first manifested as an

increase in the pulse rate and a shaking of the

muscles and limbs, followed by headaches and

delirium. This state lasts three to five hours. In

former times, the drinking of this brew was an

important part of the initiation of boys into

adulthood. Sacred songs were sung to the initiate while he was delirious. The initiate was told to

allow the visions he was going to experience to

impress themselves well upon him (Knab n.d.).

It appears that the hallucinogenic effects of

Bufo marinus were also known in Argentina, for it

is considered there to be one of the "temptations"

of Saint Anthony (see Claviceps purpurea)

(Rosemberg 1951).

Originally from the Americas, Bufo marinus

was .introduced to Australia, where it is now

known as the cane toad and its secretions are

allegedly used as a psychoactive drug. Under

Queensland's Drug Misuse Act, bufotenine is an

illegal substance in Australia (Ingram 1988,66). In

recent years, the press has been reporting

increasing cases of toad lickin' (Lyttle 1993), a

practice in which the secretions of Bufo marinus

are licked off the toad:

When licking the expressed secretions (abusers

reported that it is possible to "milk" twice a

day), a furry sensation on the lips and tongue

quickly becomes manifest. Five to ten (up to

30) minutes later, nausea is common, and only

20 to 30 minutes after ingestion, sometimes

earlier, hallucinations of various kinds set in,

beginning more rapidly and not lasting as

long as with LSD. (Keup 1995, 12)

The thickened juice of boiled animals is also

ingested in Australia (Keup 1995, 14). A decoction

of the dried skin (known as cane skin tea) is also

used (DerSpiegel32 [1994]: 92).

The secretions from Bufo marinus contain

catecholamines (dopamine, N-methyldopamine,

adrenaline, noradrenaline) and tryptamines (serotonin,

N-methyl-serotonin, bufotenine, bufotenidine,

dehydrobufotenine), as well as glycoside-like

toad toxins (Deulofeu and Ruveda 1971; Lyttle

1993, 523 f.). The skin has been found to contain

morphine. The toad toxins (bufotoxine, bufogenine,

and bufadienolides) are cardiotoxic and

are similar to digitalis in their effects: nausea,

vomiting, increase in blood pressure, confusion,

and psychotic states (Keup 1995, 12). Smoking is

probably the safest method to ingest Bufo marinus

secretions, as the burning process apparently

destroys the toxic components while leaving the

bufotenine intact (Alexander Shulgin, pers.

comm.). The ethnobotanist Brett Blosser smoked

dried Bufo marinus secretions (approximately 1

mg every few minutes) and reported experiencing

tryptamine-like hallucinations similar to those

induced by the secretions of Bufo alvarius (cf.

5-MeO-DMT) (B. Blosser, pers. comm.).

The few reports of the effects of smoked toad

skin indicate that they are hallucinogenic. One

Australian user stated, "I am seeing the world

through the consciousness of a toad" (Lewis 1989,

71).

The following species of toads contain significant

amounts of bufotenine: Bufo alvarius (cf. 5MeO-

DMT), B. americanus, B. arenarum, B. bufo

bufo, B. calamita, B. chilensis, B. crucifer, B. formosus,

B. fowleri, B. paracnemis, B. viridis (Deulofeu

and Ruveda 1971, 483).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Bufotenine is marketed as bufotenine hydrogen

oxalate. In the United States, bufotenine is classified

as a Schedule I drug (Shulgin 1981). In contrast,

in Germany it is not considered a narcotic

and is not illegal (Korner 1994, 1572*).

Literature

See also the entries for Anandenanthera colubrina

and 5-MeO-DMT.

Allen, E. R., and W. T. Neill. 1956. Effects of marine

toad toxins on man. Herpetologica 12:150-5l.

Alvarez, Ticul, and Aurelio Ocana. 1991. Restos oseos

de vertebrados terrestres de las ofrendas del

Templo Mayor, ciudad de Mexico. In La fauna en

el Templo Mayor, ed. B. Quintanar, 105-46.

Mexico City: INAH.

Chen, K. K., and H. Jensen. 1929. A pharmacognostic

study of ch'an su, the dried venom of the Chinese

toad. Journal ofthe American Pharmaceutical

Association 23:244-5l.

Davis, Wade. 1988. Bufo marinus: New perspectives

on an old enigma. Revista de la Academia

Columbiana de las Ciencies Exactas, Fisicas y

Naturales 14 (63): 151-56.

Degraaff, Robert M. 1991. The book ofthe toad.

Rochester, Vt.: Park Street Press.

Deulofeu, Venancio, and Edmundo A. Ruveda. 1971.

The basic constituents of toad venoms. In

Venomous animals and their venoms, ed.

Wolfgang Bucherl and Eleanor E. Buckley,

475-556. New York and London: Academic Press.

Fabing, Howard D., and J. Robert Hawkins. 1956.

Intravenous bufotenine injection in the human

being. Science 123:886-87.

Furst, Peter T. 1972. Symbolism and

psychopharmacology: The toad as earth mother

in Indian America. In Religion en Mesoamerica,

XII Mesa Redondo, 37-46. Mexico City: S.M.A.

---. 1981. Jaguar baby or toad mother: A new

look at an old problem in Olmec iconography. In

The Olmec and their neighbors, ed. E. Benson,

149-62. Washington, D.C.: Dumbarton Oaks.

Hamblin, Nancy 1. 1981. The magic toads of

Cozumel. Mexicon 3 (I): 10-13.

---. 1984. Animal use by the Cozumel Maya.

Tucson: The University of Arizona Press.

Hirschberg, Walter. 1988. Frosch und KrOte in Mythos

und Brauch. Vienna: Bohlau.

Hunn, Eugene S. 1977. Tzeltal folk zoology. New York:

Academic Press.

Ingram, Glen. 1988. The ''Australian'' cane toad. In

Venoms and victims, ed. John Pearn and Jeanette

Covacevich, 59-66. Brisbane: The Queensland

Museum and Amphion Press.

Kennedy, Alison B. 1982. Ecce Bufo: The toad in

nature and Olmec iconography. Current

Anthropology 23 (2): 273-90.

Keup, Wolfram 1995. Die Aga-Krote und ihr Sekret:

Inhaltsstoffe und MiBbrauch. Pharmazeutische

Zeitung 140 (42): 9-14.

Knab, Tim. n.d. Narcotic use of toad toxins in

southern Veracruz. Unpublished manuscript.

(Ten typewritten pages.)

Lewis, Stephanie. 1989. Cane toads: An unnatural

history. New York: Dolphin/Doubleday.

Lyttle, Thomas. 1993. Misuse and legend in the "toad

licking" phenomenon. The International Journal

ofthe Addictions 28 (6): 521-38.

Lyttle, Thomas, David Goldstein, and Jochen Gartz.

1996. Bufo toads and bufotenine: Fact and fiction

surrounding an alleged psychedelic. Journal of

Psychoactive Drugs 28 (3): 267-90. (Contains an

excellent bibliography.)

Mandell, A. J., and M. Morgan. 1971.

Indole(ethyl)amine N-methyltransferase in

human brain. Nature 230:85-87.

McLeod, W. R, and B. R Sitram. 1985. Bufotenine

reconsidered. Psychiatria Scandinavia 72:447-50.

Raisanen, Martti. 1985. Studies on the synthesis and

excretion of bufotenine and N,Ndimethyltryptamine

in man. Academic

dissertation, Helsinki, University of Helsinki.

Reiter, Russel J., and Jo Robinson. 1996. Melatonin.

Munich: Droemer Knaur.

Rosenberg, Tobias. 1951. El sapo en el folklore y en la

medicina. Buenos Aires: Editorial Periplo.

Shulgin, Alexander T. 1981. Bufotenine. Journal of

Psychoactive Drugs 13 (4): 389.

Taylor, Michael. 1993. The use of the Bufo marinus

toad in ancient Mesoamerica. Crash Collusion 4:

53-55.

Turner, W. J., and S. Merlis. 1959. Effects of some

indolalkylamines on man. Archives ofNeurology

and Psychiatry 81:121-29.

Verpoorte, R., Phan-Quoc-Kinh, and A. Baerheim

Svendsen. 1979. Chemical constituents of

Vietnamese toad venom collected from Bufo

melanostictus Schneider. Journal of

Ethnopharmacology 1:197-202.

Wieland, Theodor, and Werner Motzel. 1953. Dber

das Vorkommen von Bufotenin im gelben

Knollenblatterpilz. Justus Liebigs Annalen der

Chemie 581:10-16.</td>
</tr>

[gallery]

B-Phenethylamines

2013-01-13T18:43:20Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

r3-phenethylamines, PEAs, 2-phenethylamines

r3-phenethylamines are derivatives of phenethylamine

(Shulgin 1979). The biogenic 2-phenethylamine

(PEA) dilates the blood vessels in the brain

and consequently can, under certain circumstances,

cause headaches or migraines (cf. Theobroma

cacao). The most well-known psychoactive r3phenethylamine

is mescaline, a component of

numerous cacti.

Many cacti (including Gymnocactus Spp.490 and

Opuntia spp.) contain phenethylamines that are

structurally very similar to mescaline but whose

effects are practically unknown (West et al. 1974).

It is quite possible that such substances as candicine

(Trichocereus spp.), hordenine (Ariocarpus

spp., Opuntia clavata Eng.; cf. Meyer et al. 1980

and· Vanderveen et al. 1974), and macromerine

(Coryphantha spp.) produce psychoactive effects

when used at the appropriate dosages. This area

still offers many opportunities for experimental

human pharmacology (Heffter technique). Such

experimentation could, for example, lead to a

psychoactive use of the South American Notocactus

ottonis (Lehm.) Berg. [syn. Parodia ottonis]

(cf. Hecht 1995,82), a cactus that is often found at

places where cacti are sold, is very easy to grow,

and contains hordenine (Shulgin 1995, 16*). The

genus Lobivia also contains hordenine (Follas et al.

1977).

Hordenine and related substances (occasionally

in high concentrations) are also found in other

plants, such as the Himalayan Leguminosae Desmodium tiliaefolium G. Don (Ghosal and

Srivastava 1973).

Numerous phenethylamines that have psychoactive

effects (both empathogenic and/or psychedelic)

have been synthesized (e.g., MDMA, MDA,

MMDA, MDE, 2-CB, et cetera; cf. Shulgin and

Shulgin 1991*).</td>
<td valign="top" width="53%">Literature

See also the entries for mescaline.

Pallas, W. D., J. M. Cassidy, and J. 1. McLaughlin.

1977. l3-phenethylamines from the cactus genus

Lobivia. Phytochemistry 16:1459-60.

Ghosal, S., and R. S. Srivastava. 1973.I3-phenethylamine,

tetrahydroisoquinoline and indole

alkaloids of Desmodium tilaefolium.

Phytochemistry 12:193-97.

Meyer, Brian N., Yehia A. H. Mohamed, and Jerry 1.

McLaughlin. 1980. J3-phenethylamines from the

cactus genus Opuntia. Phytochemistry 19:719-20.

Shulgin, Alexander T. 1979. Chemistry of

phenethylamines related to mescaline. Journal of

Psychedelic Drugs 11 (1-2): 41-52.

Vanderveen, Randall 1., Leslie C. West, and Jerry 1.

McLaughlin. 1974. N-methyltryramine from

Opuntia clavata. Phytochemistry13:866-67.

West, Leslie G., Randell 1. Vanderveen, and Jerry 1.

McLaughlin. 1974. l3-phenethylamines from the

genus Gymnocactus. Phytochemistry 3:665-66.</td>
</tr>

Papaverine

2013-01-13T18:42:37Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisochinoline,

papaverin, papaverina, papaverine

Substance type: opium alkaloid

Papaverine is a component of opium (0.3 to 0.80/0)

and was named after the genus Papaver (cf. Papaver

somniferum). Papaverine has very weak psychoactive

properties but is a powerful vasodilator.

Effective dosages start at 200 mg. An extract of

Nuphar lutea has similar effects.

In recent years, papaverine has been used to

treat impotence, often with good success (Mellinger

et al. 1987). When used for this purpose, the substance

is injected directly into the corpus cavernosum

when the penis is flaccid (so-called SKAT

therapy; cf. Ernst et al. 1993). Among the problems

that this method may cause are painful priapism

(persistent erections for up to thirty-six hours

without sexual arousal!) and inflammation of the

penis (Sanders 1985).

Commercial Forms and Regulations

The substance, available as papaverine hydrochloride,

is sold in suppository form and in

solution for injection. Papaverine is available only

with a prescription.</td>
<td valign="top" width="53%">Literature

See also the entries for Papaver somniferum and

opium alkaloids.

Ernst, Gunter, Hans Finck, and Dieter Weinert. 1993.

Dem Manne kann geholfen werden. Munich:

Ehrenwirth.

Mellinger, Brett C., E. Darracott Vaughan, Stephen L.

Thompson, and Marc Goldstein. 1987.

Correlation between intracavernous papaverine

injection and Doppler analysis in impotent men.

Urology 30 (5): 416-19.

Porst, H. 1996. Orale und intracavernose

Pharmakotherapie. TW Urologie Nephrologie 8

(2): 88-94.

Sanders, Kevin. 1985. 30-Stunden Erektion.

Penthouse 4/85:65-68, 196, 200.

Schnyder von Wartensee, M., A. Sieber, and U. E.

Studer. 1988. Therapie der erektilen Dysfunktion

mit Papaverin-21h Jahre Erfahrung. Schweizer

medizinische Wochenschrift 118 (30): 1099-1103.</td>
</tr>

</table>

Opium Alkaloids

2013-01-13T18:41:54Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Opiate, opiates, opium compounds

The study of opium and the isolation of its constituents

ranks among the most important achievements

in the history of pharmacology (cf. Papaver

somniferum). In ancient times, opium was already

known as the best of all analgesics (cf. soporific

sponge). The isolation of morphine from opium

revolutionized pain therapy in Europe. No other

component of opium has a comparably powerful

effect. The potency of morphine would not be

exceeded until heroin (diacetylmorphine) was

synthesized (Snyder 1989). Subsequent pharmacological

research has led to the creation of

numerous morphine analogs (fentanyls), some of

which are as much as 7,500 times more potent

than morphine (Sahihi 1995,31 ff.*).

The opium alkaloids codeine and morphine

have become culturally significant as psychoactive

substances. Papaverine is used in medicine as a

treatment for impotence.

Some opium alkaloids are also found in other

Papaver species (Papaver spp.), although these

species usually contain only traces of these substances

(Khanna and Sharma 1977; Ktippers et al.

1976; Phillipson et al. 1973; Phillipson et al. 1976).

Aporphines, whose structures are analogous to

those of the opium alkaloids, occur in Papaver

fugax Poir. [syn. Papaver caucasicum M.-B., Papaver

floribundum Desf.] and Nymphaea ampla. Other

substances related to the opium alkaloids are

present in Argemone mexicana, Eschscholzia californica,

Nuphar lutea, and Papaver spp.</td>
<td valign="top" width="53%">Literature

See also the entries for Argemone mexicana, Papaver

somniferum, Papaver spp., codeine, morphine, and

papaverine.

Khanna, P., and G. 1. Sharma. 1977. Production of

opium alkaloids from in vitro tissue culture of

Papaver rhoeas 1. Indian Journal ofExperimental

Biology 15:951-52.

Krikorian, A. D., and M. C. Ledbetter. 1975. Some

observations on the cultivation of opium poppy

(Papaver somniferum 1.) for its latex. Botanical

Review 41:30-103.

Ktippers, F. J. E. M., C. A. Salmink, M. Bastart, and

M. Paris. 1976. Alkaloids of Papaver bracteatum:

Presence of codeine, neopine and alpinine.

Phytochemistry 15:444-45.

Phillipson, J. D., S. S. Handa, and S. W. EI-Dabbas.

1976. N-oxides of morphine, codeine and

thebaine and their occurrence in Papaver species.

Phytochemistry 15:1297-1301.

Phillipson, J. D., G. Sariyar, and T. Baytop. 1973.

Alkaloids from Papaver fugax of Turkish origin.

Phytochemistry 12:2431-34.

Scully, Rock, with David Dalton. 1996. An American

odyssey: Die legendare Reise von Jerry Garcia und

den Grateful Dead. St.Andra-Wordern: Hannibal

Verlag.

Snyder, Solomon H. 1989. Brainstorming: The science

and politics ofopiate research. Cambridge and

London: Harvard University Press.

The Constituents of Opium

The composition of the alkaloid mixture can

vary greatly, depending upon the strain of poppy,

the location of cultivation, and the processing

technique (Krikorian and Ledbetter 1975).

1. Isocholine derivates
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="319">codamine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">cryptopine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">gnoscopine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">hydrocotarnine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">laudanindine (= tritopine)*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">dl-Iaudanine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">laudanosine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">norlaudanosine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">narceine (= narceinum)</td>
<td valign="top" width="319">0.1-0.2%</td>
</tr>
<tr>
<td valign="top" width="319">1-narcotine (= narcotine = noscapine)</td>
<td valign="top" width="319">1-11%</td>
</tr>
<tr>
<td valign="top" width="319">oxynarcotine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">papaverine</td>
<td valign="top" width="319">0.5-10%</td>
</tr>
<tr>
<td valign="top" width="319">protopine* (also in Papaver rhoeas,</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Argemone mexicana, and</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Eschscholzia californica)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">reticuline*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">xanthaline (= papaveraldine)*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319"> </td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">II. Bases that yield phenanthrene derivatives

when broken down</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">codeine</td>
<td valign="top" width="319">0.2-4%</td>
</tr>
<tr>
<td valign="top" width="319">morphine</td>
<td valign="top" width="319">2.8-23%</td>
</tr>
<tr>
<td valign="top" width="319">neopine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">porphyroxine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">pseudomorphine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">thebaine (also in Papaver bracteatum)</td>
<td valign="top" width="319">0.1-4%</td>
</tr>
<tr>
<td valign="top" width="319">III. Other bases</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">lanthopine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">meconine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">oripavine* (also in Papaver orientale)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">papaveramine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">rhoeadine*</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Alkaloids marked with * are present in only trace

amounts.</td>
<td valign="top" width="319"> </td>
</tr>

</table>
 </td>
</tr>

</table>

N,N-DMT

2013-01-13T18:40:52Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Dimethyltryptamin, dimethyltryptamine, DMT,

nigerin, nigerina, nigerine (1946), AT,N-dimethyltryptamine,

3- [2-(dimethyl-amino)ethyl] -indole

Substance type: tryptamine (indole alkaloid)

R. H. F. Manske first created DMT as a synthetic

substance in the laboratory in 1931. It was not

until 1955 that it was isolated as a natural compound

in the seeds of Anadenanthera peregrina. It

is found in a great number of plants and also

occurs naturally in humans and other mammals

(see table, pages 853-854). N,N-DMT is closely

related to 5-MeO-DMT and psilocybin/psilocin.

N,N-DMT and 5-MeO-DMT are among the

psychedelics whose effects are short in duration.

They are not orally effective in an isolated form (as

a salt or abase) because the MAO enzyme breaks

them down before they can pass through the

blood-brain barrier (cf. ayahuasca, f3-carbolines).

They reveal their awesome effects only when

injected by syringe (Strassman et al. 1994),

snuffed, or smoked. When N,N-DMT or 5-MeODMT

is injected intravenously, the effects last

some forty-five minutes; when the substance is

smoked or snuffed, the effects last only ten

minutes. Subjectively, however, those few minutes

may seem to have spanned centuries. People who

have had experiences with DMT unanimously

agree that it is easily the most powerful psychedelic

known (cf. McKenna 1992; Meyer 1992).

Some people have described DMT as "crystallized

consciousness." When DMT is smoked, it is said

that the "scent of enlightenment" fills the air. Only

"a few seconds after taking it, DMT acts like the

trumpets of Jericho upon the gates of perception"

(Kraemer 1995, 98). DMT experiences can be so

extraordinarily alien that most subjects find it

extremely difficult or even impossible to describe

them in words. Many people speak of contact with

strange beings (aliens, fairies, machine elves, et

cetera) (Bigwood and Ott 1977; Leary 1966;

McKenna 1992; Meyer 1992).

When pure DMT is smoked or vaporized and

inhaled, the effective dosage lies around 20 mg

(although amounts as high as 100 mg are

sometimes smoked). The dosage for ayahuasca

and ayahuasca analogs ranges from 50 to 100 mg.

When DMT is injected, the typical dose is 1 mg/kg

of body weight (Ott 1993,433*).

DMT is also produced in the human nervous

system, where it appears to serve an important

function as a neurotransmitter (Barker et al. 1981;

Callaway 1996; Siegel 1995b). Neurobiologists are

as yet uncertain about the role DMT might play in

the nervous system. Hyperventilating causes the

concentration of DMT in the lungs to increase

(Callaway 1996). One physician has reported that

the release of endogenous DMT is highest at the

moment of death. It is my opinion that this

chemical messenger is responsible for the ultimate

shamanistic ecstasy, for enlightenment, and for the

merging into the "clear light of death." An experiment

in which DMT was given to practicing

Buddhists found that the subjects had experiences

and visions that corresponded to the Buddhist

teachings (Strassman 1996).

DMT has clearly inspired numerous novels in

the fantasy and science-fiction genres. The novel

Kalimantan deals with the search for a fictitious

hallucinogenic drug called seribu aso. The descriptions

of the effects of this drug agree perfectly with

the descriptions of DMT trips (Shepard 1993).

Several novels, including the Valis trilogy of the

science-fiction master Philip K. Dick (1928-1982),

also appear to represent a literary attempt to understand

the hyperdimensionality of DMT experiences

(Dick 1981a, 1981b, 1982).

Commercial Forms and Regulations

DMT occurs as a free base, an HCL, and a

fumarate. Although the fumarate crystallizes out

easily, it contains only 600/0 of the pure substance.

DMT is classified as a Schedule I drug in the

United States and is a "narcotic drug in which

trafficking is not allowed" in Germany as well as in

Switzerland (Korner 1994,38*).</td>
<td valign="top" width="53%">Plants Containing DMT

(from Block 1994*; Smith 1977; Montgomery, pers. comm.; Ott 1993*; Schultes and Hofman 1980,

155*; supplemented)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="319">Species</td>
<td valign="top" width="319">Demonstrated Tryptamines</td>
</tr>
<tr>
<td valign="top" width="319">AGARICACEAE (FuNGI)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Amanita citrina Gray</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Amanita porphyria (Fries) Secretan</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Amanita spp.</td>
<td valign="top" width="319">DMT, bufotenine</td>
</tr>
<tr>
<td valign="top" width="319">AIZOACEAE/MESEMBRYANTHEMACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Delosperma sp.</td>
<td valign="top" width="319">DMT,MMT</td>
</tr>
<tr>
<td valign="top" width="319">Mesembryanthemum spp.</td>
<td valign="top" width="319">DMT (?)</td>
</tr>
<tr>
<td valign="top" width="319">GRAMINEAE (POACEAE)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Arundo donax 1.</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Phalaris arundinacea 1.</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Phalaris tuberosa 1.</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Phragmites australis (Cav.) Trin. ex Steud.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">LAURACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Umbellularia californica (Hook. et A.) Nutt.</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">LEGUMINOSAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Acacia confusa Merr.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Acacia maidenii F. von Mue1!.</td>
<td valign="top" width="319">DMT (0.360/0)</td>
</tr>
<tr>
<td valign="top" width="319">Acacia nubica Benth.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Acacia phlebophylla F. von Mue1!.</td>
<td valign="top" width="319">0.30/0 DMT</td>
</tr>
<tr>
<td valign="top" width="319">Acacia simpIicifolia Druce</td>
<td valign="top" width="319">0.810/0 DMT</td>
</tr>
<tr>
<td valign="top" width="319">Acaciaspp.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Anadenanthera colubrina (VeIl.) Bren.</td>
<td valign="top" width="319">DMT, 5-MeO-DMT, bufotenine</td>
</tr>
<tr>
<td valign="top" width="319">Anadenanthera peregrina (1.) Spag.</td>
<td valign="top" width="319">DMT, 5-MeO-DMT, bufotenine</td>
</tr>
<tr>
<td valign="top" width="319">Desmanthus illinoensis (Michx.) MacMillan</td>
<td valign="top" width="319">DMT (to 0.340/0)</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium adscendens (Sw.) DC. var. adscendens</td>
<td valign="top" width="319">DMT (?)</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium caudatum DC.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium gangeticum DC.</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium gyrans DC.</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium pulchellum Benth. ex Bak.</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium racemosum Thunb.</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium tiliaefolium G. Don</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Desmodium triflorum DC.</td>
<td valign="top" width="319">DMT, bufotenine, and others</td>
</tr>
<tr>
<td valign="top" width="319">Lespedeza bicolor Turcz.</td>
<td valign="top" width="319">DMT, 5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Lespedeza bicolor var. japonica Nakai</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Lespedeza capitata Michx.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Mimosa scabrella Benth.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Mimosa tenuiflora (Willd.) Pair. [syn. Mimosa hostilis</td>
<td valign="top" width="319">0.570/0 DMT</td>
</tr>
<tr>
<td valign="top" width="319">Benth., Mimosa nigra]</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Mimosa verrucosa</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Mimosaspp.</td>
<td valign="top" width="319">DMT and others</td>
</tr>
<tr>
<td valign="top" width="319">Mucuna pruriens DC.</td>
<td valign="top" width="319">DMT, 5-MeO-DMT, bufotenine</td>
</tr>
<tr>
<td valign="top" width="319">Mucunaspp.</td>
<td valign="top" width="319">DMT and others</td>
</tr>
<tr>
<td valign="top" width="319">Petalostylis cassioides Pritze1</td>
<td valign="top" width="319">DMT, tetrahydroharmane</td>
</tr>
<tr>
<td valign="top" width="319">Petalostylis labicheoides R. Brown</td>
<td valign="top" width="319">DMT, tryptamine</td>
</tr>
<tr>
<td valign="top" width="319">Phyllodium pulchellum (1.) Desv.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">MALPIGHIACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Banisteriopsis argentea Spring. [syn. B. muricata (Cav.) Cuatr.]</td>
<td valign="top" width="319">DMT, DMT</td>
</tr>
<tr>
<td valign="top" width="319">Diplopterys cabrerana (Cuatr.) Gates</td>
<td valign="top" width="319">DMT,5</td>
</tr>
<tr>
<td valign="top" width="319">[syn. Banisteriopsis rusbyana]</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">MYRISTICACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Iryanthera ulei Warb.</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Osteophloeum platyspermum (DC.) Warb.</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Viroia calophylla Warb.</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola calophylloidea Markgr.</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola carinata (Spruce ex Benth.) Warb.</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola divergens Ducke</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola elongata (Spruce ex Benth.) Warb.</td>
<td valign="top" width="319">DMT, 5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola melinonii (Benoist) A.C. Smith</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola multinerva Ducke</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola pavonis (DC.) A.C. Smith</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola peruviana (DC.) Warb.</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola rufula (DC.) Warb.</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola sebifera Aubi.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola theiodora (Spruce ex Benth.) Warb.</td>
<td valign="top" width="319">DMT,5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Virola venosa (Benth.) Warb.</td>
<td valign="top" width="319">DMT, 5-MeO-DMT, and others</td>
</tr>
<tr>
<td valign="top" width="319">Virolaspp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">OCHNACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Testulea gabonensis Pellegr.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">POLYGONACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Eriogonum sp.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">RUBIACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Psychotria carthaginensis Jacq.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Psychotria poeppigiana Mueli. Arg.</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Psychotria viridis Ruiz et Pay. [syn. P. psychotriaefolia Stand!.]</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">RUTACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Dictyoloma incanescens DC.</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Dutaillyea drupacea (Baill.) Hartley</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Dutaillyea oreophila (Baill.) Sevenet-Pusset</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Evodia rutaecarpa Benth.</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Limonia acidissima 1.</td>
<td valign="top" width="319">DMT traces</td>
</tr>
<tr>
<td valign="top" width="319">Melicope leptococca (Baill.) Guill.</td>
<td valign="top" width="319">0.21% DMT</td>
</tr>
<tr>
<td valign="top" width="319">Pilocarpus organensis Rizzini et Occhioni</td>
<td valign="top" width="319">5-MeO-DMT</td>
</tr>
<tr>
<td valign="top" width="319">Vepris ampody H. Perro</td>
<td valign="top" width="319">DMT</td>
</tr>
<tr>
<td valign="top" width="319">Zanthoxylum arborescens Rose</td>
<td valign="top" width="319">DMT traces</td>
</tr>
<tr>
<td valign="top" width="319">Zanthoxylum procerum Donn. Sm.</td>
<td valign="top" width="319">DMT</td>
</tr>

</table>
 Literature

See also the entries for 5-MeO-DMT.

Arnold, O. H., and G. Hofman. 1957. Zur

Psychopathologie des Dimethyltryptamine.

Wiener Zeitschrift fur Nervenheilkunde 13:438-45.

Barker, S., J. Monti, and S. Christian. 1981. N,Ndimethyltryptamine:

An endogenous

hallucinogen. International Review of

Neurobiology 22:83-110.

Bigwood, Jeremy, and Jonathan Ott. 1977. DMT: The

fifteen minute trip. Head 11:56 ff.

Callaway, James. 1996. DMTs in the human brain. In

Yearbook for Ethnomedicine and the Study of

Consciousness (1995), 4:45-54. Berlin: VWB.

Dick, Philip K. 1981a. The divine invasion, New York:

Vintage Books.

---. 1981b. Valis. New York: Vintage Books.

---. 1982. The transmigration of Timothy Archer.

New York: Vintage Books.

Kraemer, Olaf. 1995. Die Trompeten Jerichos. Wiener

9:97-99.

Lamparter, Daniel, and Adolf Dittrich. 1996. Intraindividuelle

Stabilitat von ABZ unter sensorischer

Deprivation, N,N-Dimethyltryptamin (DMT)

und Stickoxydul. In Jahrbuch des Europiiischen

Collegiums fur Bewufitseinsforschung (1995),

33-43. Berlin: VWB.

Leary, Timothy. 1966. Programmed communication

during experience with DMT. Psychedelic Review

8:83-95.

Manske, R. H. F. 1931. A synthesis of the methyltryptamines

and some derivatives. Canadian

Journal ofResearch 5:592-600.

McKenna, Terence. 1992. Tryptamin hallucinogens

and consciousness. In Yearbook for Ethnomedicine

and the Study ofConsciousness (1992),1:133-48.

Berlin: VWB.

Meyer, Peter. 1992. Apparent communication with

discarnate entities induced by dimethyltryptamine

DMT. In Yearbook for Ethnomedicine and the Study

ofConsciousness (1992),1:149-74. Berlin: VWB.

Shepard, Lucius. 1993. Kalimantan. New York: Tom

Doherty Associates.

Shulgin, Alexander T. 1976. Profiles of psychedelic

drugs. 1: DMT. Journal ofPsychedelic Drugs 8 (2):

167-68.

Smith, Terence A. 1977. Tryptamine and related

compounds in plants. Phytochemistry 16:171-75.

Strassman, Rick J. 1996. Sitting for sessions: Dharma

and DMT research. Tricycle 6 (1): 81-88.

Strassman, Rick J., Clifford R. Qualls, Eberhard H.

Uhlenhuth, and Robert Kellner. 1994. Doseresponse

study of ~N-dimethyltryptaminin

humans. Archive of General Psychiatry 51:85-97,

98-108.

Szara, S. 1. 1956. Dimethyltryptamin: Its metabolism

in man; the relation of its psychotic effect to the

serotonin metabolism. Experientia 15 (6): 441-42.</td>
</tr>

</table>

Nicotine

2013-01-13T18:39:46Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Nicotin, nikotin, (-) -nikotin , 1-methyl-2(3-pyridyl)pyrrolidine,

3-( 1-methyl-2-pyrrolidinyl)pyridine

Substance type: pyrrolidine alkaloid, pyridine alkaloid,

tobacco alkaloid

Nicotine was first discovered in tobacco (Nicotiana

tabacum) and was named for the genus. It

occurs in numerous species of Nicotiana as well as

other members of the Nightshade Family. It has

also been found in club moss (Lycopodium

clavatum).

Nicotine is very easily absorbed through the

mucous membranes and even through the skin.

Consequently, plants that contain nicotine can be

smoked or administered as enemas. Nicotine is

broken down through oxidation, and about 100/0 is

excreted unchanged. It has stimulating effects

upon the central nervous system and has paralyzing

effects at very high dosages (cf. cytisine). In

the peripheral nervous system, nicotine behaves in

a similar manner as the neurotransmitter acetylcholine.

High dosages can result in sudden death

due to respiratory paralysis or cardiac arrest

within five minutes of ingestion (Roth et al. 1994,

864*). From 40 to 60 mg represents a lethal dosage

for humans (Frerichs, Arends, Zarnig, Hagers

Handbuch). Diazepam can be effective as an

antidote for nicotine poisoning (Roth et al. 1994,

865*). Nicotine is now generally regarded as

highly "addictive" (Schiffman 1981). Although it is

commonly assumed that nicotine causes cancer,

uncertainty has been expressed about this theory

(Schievelbein 1972).

Nicotine has been detected in Egyptian rnummies

(New Kingdom) (Balabanova et al. 1992*).

However, this discovery should not be taken as

evidence that the Egyptians knew of wild tobacco

(Nicotiana rustica) , as the Balabanova team in

Munich has suggested, for some Old World plants

also contain nicotine (see the table at right).

Commercial Forms and Regulations

Nicotine can be obtained in its pure form from

chemical suppliers. It is subject to the laws

covering the transport of dangerous substances

and is classified as a Category 1 substance on the

Swiss Poison List. In the United States, pure

nicotine is available only with a prescription (Ott

1993, 447*). In Germany, it is subject to the laws

regarding dangerous substances but is not

regarded as a "narcotic."</td>
<td valign="top" width="53%">Plants Containing Nicotine

(from Bock 1994,93*; Rampp 1995,2995*;

Schultes and Raffauf 1991, 37*; supplemented)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="319">Stock Plant</td>
<td valign="top" width="319">Plant Part(s)</td>
</tr>
<tr>
<td valign="top" width="319">ARACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Arum maculatum 1.</td>
<td valign="top" width="319">herbage</td>
</tr>
<tr>
<td valign="top" width="319">(cuckoo pint)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">ASCLEPIADACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Asclepias syriaca 1.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">(Syrian milkweed)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">EQUISETACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Equisetum palustre 1.</td>
<td valign="top" width="319">herbage</td>
</tr>
<tr>
<td valign="top" width="319">(marsh horsetail; cf.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Equisetum arvense)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">ERYTHROXYLACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Erythroxylum coca</td>
<td valign="top" width="319">roots, stems</td>
</tr>
<tr>
<td valign="top" width="319">Erythroxylum spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">LEGUMINOSAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Acacia retinodes Schlechtend.</td>
<td valign="top" width="319">leaves</td>
</tr>
<tr>
<td valign="top" width="319">(cf. Acacia spp.)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Mucuna pruriens</td>
<td valign="top" width="319">leaves</td>
</tr>
<tr>
<td valign="top" width="319">LYCOPODIACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Lycopodium spp. (club moss;</td>
<td valign="top" width="319">herbage</td>
</tr>
<tr>
<td valign="top" width="319">cf. Trichocereus pachanoi)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">SOLANACEAE (NIGHTSHADES)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Cestrum spp. (cf. Cestrum ,</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">nocturnum Cestrum parqui)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Cyphomandra spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Datura metel</td>
<td valign="top" width="319">herbage</td>
</tr>
<tr>
<td valign="top" width="319">Duboisia hopwoodii</td>
<td valign="top" width="319">leaves</td>
</tr>
<tr>
<td valign="top" width="319">Duboisia spp.</td>
<td valign="top" width="319">leaves, bark</td>
</tr>
<tr>
<td valign="top" width="319">Nicotiana rustica</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Nicotiana tabacum</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Nicotiana spp.</td>
<td valign="top" width="319"> </td>
</tr>

</table>
 Literature

See also the entries for Nicotiana rustica, Nicotiana

tabacum, and Nicotiana spp.

Lee, Richard S., and Mary Price Lee. 1994. Caffeine

and nicotine. New York: The Rosen Publishing

Group.

Schievelbein, H. 1972. Biochemischer

Wirkungsmechanismus des Nikotins oder seiner

Abbauprodukte hinsichtlich eines eventuellen

carcinogenen, mutagenen oder teratogenen

Effektes. Planta Medica 22:293-305.

Shiffman, Saul. 1981. Tabakkonsum und

Nikotinabhangigkeit. In Rausch und Realitiit, ed.

G. Volger, 2:780-83. Cologne: RautenstrauchJoest-

Museum fur Volkerkunde.</td>
</tr>

</table>

Muscimol

2013-01-13T18:37:30Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Agarin, 5-(aminomethyl)-3- [2H] -isoxazolone, pyroibotenic

acid, 3-hydroxy-5-aminomethyl-isoxazole

Substance type: amino acid, isoxazole derivative

Muscimol was first described in 1964 as a constituent

of Amanita pantherina. Muscimol is the

decarboxylated product of ibotenic acid and is

considered to be more psychoactive than it. Some

15 to 20 mg is regarded as a psychoactive dosage

(Muller and Eugster 1965; Ott 1993,446*; Scotti et

al. 1969).

Muscimol is an analog of the neurotransmitter

GABA (gamma amino butyric acid) and docks to

its receptor (Johnston 1971). Kavapyrones (cf.

Piper methysticum) also bind to the same receptor.

Ibotenic acid as well as muscimol were detected

in the urine of people who had eaten fly agaric

mushrooms (Amanita muscaria) about an hour

earlier. An experiment with mice conducted by the

same team of researchers found that the amount of

active constituents in the urine passed by one

inebriated animal was not sufficient to inebriate

another animal (Ott et al. 1975).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Muscimol can be purchased from chemical suppliers.

The substance is legal and is not subject to

any specific regulations.



Literature

See also the entries for Amanita muscaria and

ibotenic acid.

Johnston, G. A. R. 1971. Muscimol and the uptake of

,),-aminobutyric acid by rat brain slices.

Psychopharmacologia 22:230.

Muller, G. F. R., and C. H. Eugster. 1965. Muscimol,

ein pharmakodynamisch wirksamer Stoff aus

Amanita muscaria. Helvetica Chemica Acta

48:910-26.

Ott, Jonathan, Preston S. Wheaton, and William

Scott Chilton. 1975. Fate of muscimol in the

mouse. Physiol. Chem. and Physics 7:381-84.

Scotti de Carolis, A., et al. 1969.

Neuropharmacological investigations on

muscimol, a psychotropic drug extracted from

Amanita muscaria. Psychopharmacologia

15:186-95.</td>
</tr>

</table>

Morphine

2013-01-13T18:36:33Z

205.56.181.196:

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

4,5a-epoxy-17-methyl-7-morphinen-3,6a-diol,

morfina, morphin, morphinium, morphium

Substance type: opium alkaloid

Sometime around 1803 and 1804, Friedrich

Wilhelm Adam Serturner (1783-1841), a

pharmacist's assistant, first isolated morphine as

the "sleep-inducing principle" in opium (cf.

Papaver somniferum, opium alkaloids). This

achievement was the most important "quantum

leap" in the history of pharmacology and represents the beginning of the true chemical investigation

of plants. Today, the Serturner Medal is still

awarded for exceptional work in pharmaceutics.

Morphine may also be present in Papaver

decaisnei Hochst., Papaver dubium 1. [syn. Papaver

modestum Jordan, Papaver obtusifolium Desf.],

and Papaver hybridum 1. (Slavik and Slavikova

1980). Whether morphine occurs in Argemone

mexicana and other Papaver species (Papaver

spp.) is doubtful, while the idea that hops (Humulus

lupulus) contains morphine is a figment of

someone's imagination. Tiny traces of the

substance have been found in hay and lettuce (cf.

Lactuca virosa) (Amann and Zenk 1996, 19).

Morphine has also been detected in the skin of Bufo marinus toads (cf. bufotenine) (Amann and

Zenk 1996, 18).

Since the time when morphine was first

detected in breast milk, cow's milk, and human

cerebrospinal fluid, it has been known that it is a

natural endogenous neurotransmitter in higher

vertebrates, including humans (Amann and Zenk

1996; Cardinale et al. 1987; Hazum et al. 1981).

Morphine does not bind well to the encephalin

receptors (to which the endorphins dock) but

docks at the specific morphine (m) receptors

(Hazum et al. 1981). It is most likely biosynthesized

in the body from dopamine (Brossi 1991).

Another closely related substance, codeine, is also

endogenous in humans (Cardinale et al. 1987).

Morphine is the best and strongest natural

painkiller known. Its efficaciousness is surpassed

only by that of the synthetic morphine analogs

(heroin, fentanyl). Morphine is particularly well

suited for treating chronic pain, such as in cancer

therapy (Amann and Zenk 1996; Melzack 1991).

Endogenous morphine constitutes the body's own

pain medication:

Studies on rats have shown that among

animals who were suffering from arthritis,

morphine concentrations in the spinal cord

and urine were significantly elevated. Because

of this, it is assumed today that the organism

produces increased amounts of morphine in

certain disease states. Consequently, endogenous

morphine may serve to regulate pain

in the organism. Morphine exists in animal

and human tissue and is excreted in significant

amounts in the urine. (Amann and Zenk

1996,24)

About 30 mg orally represents an effective

dosage. Habitual morphine users may use as much

as 1 g per day (Hirschfeld and Linsert 1930,255*):

It is known that opium eaters experience a

significant increase in sexual functions during

the initial period of opium consumption.

During opium inebriation, erotic images

appear and may even include extraordinary

sexual fantasies.... The effects of morphine

are similar, where an increase in sexual

excitability was observed following several

weeks of taking 0.03 to 0.06 g per day. (Max

Marcuse, 1923, Handworterbuch der Sexualwissenschaft

[Handbook of Sexual Sciences] )

When used for sedation, in anesthesia, and for

calming and antispasmodic purposes, pharmaceutical

preparations of morphine hydrochloride and

atropine sulfate or morphine hydrochloride and scopolamine

hydrobromide are used-the final

reminders of the recipes for the former soporific

sponges.

During the Golden Twenties, the use of morphine

in Berlin society circles was depicted in

numerous pictures and illustrations (e.g., by Paul

Kamm) that appeared in magazines. These illustrations

played a great role in creating the stereotype

of the "Morphinist" (cf. Papaver somniferum),

who also became the object of literary treatments

(Bulgaka 1971; Mac From 1931). Even the life

story of the man who first discovered the substance,

Friedrich Wilhelm Sertiirner, became the

subject of a novel (Schumann-Ingolstadt n.d.).

Heroin, a derivative of morphine, has also inspired

a rich body of literature. One of the first of this

was the novel Heroin, by Rudolf Brunngraber

(1952*), which dealt with the role of heroin in

Egypt during the Golden Twenties.

Morphine was and still is a popular inebriant

in the music scene (particularly that of jazz and

rock). "Sister Morphine," a song by the Rolling

Stones (Sticky Fingers, Virgin Records, 1971), is

arguably the most famous hymn to the drug.

Morphine, a crossover band that mixes elements

of cool jazz and modern rock, took its name from

the alkaloid, and one of its albums is titled Cure for

Pain (Rykodisc, 1993).</td>
<td valign="top" width="53%"></td>
</tr>

</table>

Morphine

2013-01-13T18:34:18Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

4,5a-epoxy-17-methyl-7-morphinen-3,6a-diol,

morfina, morphin, morphinium, morphium

Substance type: opium alkaloid

Sometime around 1803 and 1804, Friedrich

Wilhelm Adam Serturner (1783-1841), a

pharmacist's assistant, first isolated morphine as

the "sleep-inducing principle" in opium (cf.

Papaver somniferum, opium alkaloids). This

achievement was the most important "quantum

leap" in the history of pharmacology and represents the beginning of the true chemical investigation

of plants. Today, the Serturner Medal is still

awarded for exceptional work in pharmaceutics.

Morphine may also be present in Papaver

decaisnei Hochst., Papaver dubium 1. [syn. Papaver

modestum Jordan, Papaver obtusifolium Desf.],

and Papaver hybridum 1. (Slavik and Slavikova

1980). Whether morphine occurs in Argemone

mexicana and other Papaver species (Papaver

spp.) is doubtful, while the idea that hops (Humulus

lupulus) contains morphine is a figment of

someone's imagination. Tiny traces of the

substance have been found in hay and lettuce (cf.

Lactuca virosa) (Amann and Zenk 1996, 19).

Morphine has also been detected in the skin of Bufo marinus toads (cf. bufotenine) (Amann and

Zenk 1996, 18).

Since the time when morphine was first

detected in breast milk, cow's milk, and human

cerebrospinal fluid, it has been known that it is a

natural endogenous neurotransmitter in higher

vertebrates, including humans (Amann and Zenk

1996; Cardinale et al. 1987; Hazum et al. 1981).

Morphine does not bind well to the encephalin

receptors (to which the endorphins dock) but

docks at the specific morphine (m) receptors

(Hazum et al. 1981). It is most likely biosynthesized

in the body from dopamine (Brossi 1991).

Another closely related substance, codeine, is also

endogenous in humans (Cardinale et al. 1987).

Morphine is the best and strongest natural

painkiller known. Its efficaciousness is surpassed

only by that of the synthetic morphine analogs

(heroin, fentanyl). Morphine is particularly well

suited for treating chronic pain, such as in cancer

therapy (Amann and Zenk 1996; Melzack 1991).

Endogenous morphine constitutes the body's own

pain medication:

Studies on rats have shown that among

animals who were suffering from arthritis,

morphine concentrations in the spinal cord

and urine were significantly elevated. Because

of this, it is assumed today that the organism

produces increased amounts of morphine in

certain disease states. Consequently, endogenous

morphine may serve to regulate pain

in the organism. Morphine exists in animal

and human tissue and is excreted in significant

amounts in the urine. (Amann and Zenk

1996,24)

About 30 mg orally represents an effective

dosage. Habitual morphine users may use as much

as 1 g per day (Hirschfeld and Linsert 1930,255*):

It is known that opium eaters experience a

significant increase in sexual functions during

the initial period of opium consumption.

During opium inebriation, erotic images

appear and may even include extraordinary

sexual fantasies.... The effects of morphine

are similar, where an increase in sexual

excitability was observed following several

weeks of taking 0.03 to 0.06 g per day. (Max

Marcuse, 1923, Handworterbuch der Sexualwissenschaft

[Handbook of Sexual Sciences] )

When used for sedation, in anesthesia, and for

calming and antispasmodic purposes, pharmaceutical

preparations of morphine hydrochloride and

atropine sulfate or morphine hydrochloride and scopolamine

hydrobromide are used-the final

reminders of the recipes for the former soporific

sponges.

During the Golden Twenties, the use of morphine

in Berlin society circles was depicted in

numerous pictures and illustrations (e.g., by Paul

Kamm) that appeared in magazines. These illustrations

played a great role in creating the stereotype

of the "Morphinist" (cf. Papaver somniferum),

who also became the object of literary treatments

(Bulgaka 1971; Mac From 1931). Even the life

story of the man who first discovered the substance,

Friedrich Wilhelm Sertiirner, became the

subject of a novel (Schumann-Ingolstadt n.d.).

Heroin, a derivative of morphine, has also inspired

a rich body of literature. One of the first of this

was the novel Heroin, by Rudolf Brunngraber

(1952*), which dealt with the role of heroin in

Egypt during the Golden Twenties.

Morphine was and still is a popular inebriant

in the music scene (particularly that of jazz and

rock). "Sister Morphine," a song by the Rolling

Stones (Sticky Fingers, Virgin Records, 1971), is

arguably the most famous hymn to the drug.

Morphine, a crossover band that mixes elements

of cool jazz and modern rock, took its name from

the alkaloid, and one of its albums is titled Cure for

Pain (Rykodisc, 1993).</td>
<td valign="top" width="53%">Cacti Containing Mescaline

(from Doetsch et al. 1980; La Barre 1979; Mata and McLaughlin 1982*; Shulgin 1995*; Lundstrom

1971; Pardanini et al. 1978; Ott 1993*; Turner and Heyman 1960)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="213">Species</td>
<td valign="top" width="213">Occurrence</td>
<td valign="top" width="213">Use</td>
</tr>
<tr>
<td valign="top" width="213">Gymnocalycium gibbosum (Haw.) Pfeiffer</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Gymnocalycium leeanum (Hook.) Br. et R.</td>
<td valign="top" width="213">Argentina, Uruguay</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Islaya minor Backeb.</td>
<td valign="top" width="213">southern Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Lophophora diffusa (Croizat) Bravo</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213">peyote substitute</td>
</tr>
<tr>
<td valign="top" width="213">[syn. Lophophora echinata]</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Lophophora jourdaniana [nom. nud.]</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Lophophora williamsii (Lem.) Coult.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">[syn. Lophophora fricii Habermann]</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Myrtillocactus geometrizans (Mart.) Cons.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia acanthocarpa Engelm. et Bigel.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia basilaria Engelm. et Bigel.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia cylindrica (Lam.) S.-D.</td>
<td valign="top" width="213">Chile</td>
<td valign="top" width="213">inebriant502</td>
</tr>
<tr>
<td valign="top" width="213">Opuntia echinocarpa Engelm. et Bigel.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia ficus-indica (L.) Mill.</td>
<td valign="top" width="213">Mexico, Egypt503</td>
<td valign="top" width="213">food</td>
</tr>
<tr>
<td valign="top" width="213">Opuntia imbricata (Haw.) DC.</td>
<td valign="top" width="213">Arizona</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia spinosior (Engelm.) Tourney</td>
<td valign="top" width="213">Arizona</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pelecyphora aselliformis Ehrenb.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213">peyote substitute</td>
</tr>
<tr>
<td valign="top" width="213">Pereskia corrugata Cutak</td>
<td valign="top" width="213">Florida</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pereskia tampicana Web.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pereskiopsis scandens Br. et R.</td>
<td valign="top" width="213">Yucatan</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Polaskia chende (Gossel.) Gibs.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Polaskia sp.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pterocereus gaumeri (Br. et R.) Mac-Doug. et Mir.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pterocereus sp.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus beneckei (Ehrenb.) Buxbaum</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus eruca (Brand.) Gibs. et Horak</td>
<td valign="top" width="213">Baja California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus stellatus (Pfeiffer) Rice</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus treleasei (Br. et R.) Backeb.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus sp.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stetsonia coryne (SD.) Br. et R.</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus bridgesii (SD.) Br. et R.</td>
<td valign="top" width="213">Peru, Bolivia</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus cuscoensis Br. et R.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus fulvinanus Ritt.</td>
<td valign="top" width="213">Chile</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus macrogonus (SD.) Ricc.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus pachanoi Br. et R.</td>
<td valign="top" width="213">Peru, Ecuador</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus peruvianus Br. et R.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus spachianus (Lem.) Rice.</td>
<td valign="top" width="213">Indiana (cultivated)</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus strigosus (SD.) Br. et R.</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus taquimbalensis Card.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus terscheckii (Parm.) Br. et R.</td>
<td valign="top" width="213">Peru, northwestern</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus validus (Monv.) Backbg.</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus werdermannianus Backbg.</td>
<td valign="top" width="213">Peru, Bolivia</td>
<td valign="top" width="213"> </td>
</tr>

</table>
Commercial Forms and Regulations

Morphine is available from pharmacies in the

form of morphine hydrochloride. Although morphine

is covered by narcotics laws, it can be

obtained with a special prescription. In the United

States, morphine is a Schedule II substance.



Literature

See also the entries for Papaver somniferum and

Papaver spp.

Amann, Tobias, and Meinhart H. Zenk. 1996.

Endogenes Morphin: Schmerzmittelsynthese in

Mensch und Tier. Deutsche Apotheker Zeitung 136

(7): 17-25. (Contains a very good bibliography.)

Brossi, Arnold. 1991. Mammalian alkaloids:

Conversions of tetrahydroisoquinoline-1carboxylic

acid derived from dopamin. Planta

Medica 57 suppl. (1): 93 ff.

Bulgaka, M. 1971. Morphium Erzahlungen. Zurich:

Arche Verlag.

Cardinale, George J., Josef Donnerer, A. Donald

Finck, Joel D. Kantrowitz, Kazuhiro Oka, and

Sydney Spector. 1987. Morphine and codeine are

endogenous compounds of human cerebrospinal

fluid. Life Sciences 40:301-6.

Fairbain, J. W., S. S. Handa, E. Giirkan, and J. D.

Phillipson. 1978. In vitro conversion of morphine

to its N-oxide in Papaver somniferum latex.

Phytochemistry 172:261-62.

Ferres, H. 1926. Gefahrliche Betaubungsmittel:

Morphium und Kokain. In Bibliothek der

Unterhaltung und des Wissens, 5:136-44.

Stuttgart: Union Deutsche Verlagsgesellschaft.

Hazum, Eli, Julie J. Sabatka, Kwen-Jen Chang, David

A. Brent, John W. A. Findlay, and Pedro

Cuatrecasas. 1981. Morphine in cow and human

milk: Could dietary morphine constitute a ligand

for specific morphine (m) receptors? Science

213:1010-12.

Kramer, John C. 1980. The opiates: Two centuries of

scientific study. Journal ofPsychedelic Drugs 12

(2): 89-103.

Mac From, ed. 1931. Taglich 5 Gramm MorphiumAufzeichnungen

eines Morphinisten. BerlinPankow:

A. H. Muller.

Melzack, Ronald. 1991. Morphium und schwere

chronische Schmerzen. Offprint of Spektrum der

Wissenschaft. Heidelberg: Spektrum der

Wissenschaft Verlag.

Schmitz, Rudolf. 1983. Friedrich Wilhelm A.

Serturner und die Morphinentdeckung.

Pharmazeutische Zeitung 128:1350-59.

Schuhmann-Ingolstadt, Otto. n.d. Morphium:

Lebensroman des Entdeckers. Berlin and

Frankfurt/M.: Deutscher Apothekerverlag.

Slavik. J., and 1. Slavikov<i. 1976. Occurrence of

morphin as a minor alkaloid in Papaver decaisnei

Hochst. Collection Czechoslov. Chem. Commun.

45:2706-9.</td>
</tr>

</table>

Mescaline

2013-01-13T18:33:21Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Mescalin, meskalin, mezcalin, mezkalin, 3,4,5-trimethoxy-

benzolmethanamine, 3,4,S-trimethoxyf3-

phenethylamine, 3,4,5-trimethoxyethyl- phenylamine,

TMPFA, 2-(3,4,S-trimethoxy-phenyl)ethylamine

Empirical formula: CllH17N03

Substance type: lophophora alkaloid, f3-phenethylamine

Mescaline was first isolated in 1886 from "mescal

buttons;' the aboveground parts of the peyote

cactus (Lophophora williamsii), and was named

after them. Mescaline is the most thoroughly

studied of all psychoactive plant constituents. In

the period between 1886 and 1950, more than one

hundred mescaline research studies were published

in the German language alone (Passie

1994). This alkaloid was found to be a component

of numerous cacti (see the table on page 847). And

it is possible that mescaline is produced from

dopamine in vitro (Paul et al. 1969; Rosenberg et

al. 1969).

Arthur Heffter was the first person to initially

test an isolated plant constituent on himself (Heffter

1894). The classic Heffter dosage consisted of 150

mg mescaline hydrochloride (HCL). A psychedelic

dosage is now considered to be 178 to 256 mg of

mescaline HCL or 200 to 400 mg of mescaline

sulfate. The highest measured dosage reported in

the literature was 1,500 mg. Taken orally,S mg/kg

of pure mescaline is regarded as a hallucinogenic

dosage. In the toxicological literature, there is no

known lethal dosage of mescaline when it is

ingested orally (Brown and Malone 1978, 14).

Western psychiatry has been aware of

consciousness-altering drugs since the nineteenth

century. Mescaline was the first substance to be

tested and applied in psychiatry. At the time,

researchers regarded the effects of mescaline on a healthy subject as inducing a state that was otherwise

known only in psychopathic patients. This

led to the idea of pharmacologically induced

"model psychoses" (Leuner 1962*). The effects of

mescaline (and also of psilocybin) were described

as "intoxication, toxic ecstasy, clouding of consciousness,

hallucinosis, model psychosis, drug

intoxication, emphasis, daydream;' et cetera

(Passie 1994). Only in recent years has there been a

shift in thinking away from the model psychosis

concept and a recognition that psychedelic states

and psychoses do not have a common origin

(HermIe et al. 1988*, 1992*, 1993*).

The predominant effects of mescaline are a

"reveling of the individual senses and primarily

visual orgies" (Ellis 1971, 21). The mescaline

inebriation was first systematically described by

Kurt Beringer in 1927. To date, there have been

many encounters with the substance, and the most

commonly reported experiences are ecstatic and

visionary in nature:

My awareness of subject and object

disappeared, and I felt dissolved, rising in an

orchestra of sounds. This ecstatic state was

accompanied by an indescribable sensation of

happiness. (Ammon and Gotte 1971,32)

It has often been suggested that pure mescaline

can be taken in place of Lophophora williamsii.

"However, most peyote users are of the opinion

that synthetic mescaline cannot be compared with

the effects of peyote" (Harp 1996, 16).

On the Cultural History of Mescaline

Aldous Huxley (1894-1963) made the psychedelic

effects of mescaline famous in his two essays "The

Doors of Perception" and "Heaven and Hell:'

Usually the person taking mescaline will

discover an inner world that is so obviously

something given, so enlighteningly eternal

and sacred, as the transformed outer world

that I had perceived with my eyes open.

(Huxley 1970,32*)

It is very likely that Hermann Hesse also had

contact with mescaline, and that it may have

inspired his novel SteppenwolJ, one of the cult

books of the hippie generation. The psychedelic

rock band Steppenwolf took its name from the

book, and the novel also became a motion picture

starring Max von Sydow (USA 1974).

Nationalgalerie, a German New Wave band,

sings on its album Mescaline, "To be transformed by a trickster fairy. My lawyer advised me to take

some mescaline" (Sony Records, 1995).

The French novelist and artist Henri Michaux

(1899-1984) studied mescaline during the 1960s

and ingested it to see what effects it might have

upon his creativity. Like many other FrenchJmen,

however, he summarized his experience as an

"accursed miracle" and scribbled his experiences of inner turmoil on paper (Michaux 1986). Today,

these "drawings" are still reproduced in publications

as an example of the "psychosis-like"

effects of mescaline.

 </td>
<td valign="top" width="53%">Cacti Containing Mescaline

(from Doetsch et al. 1980; La Barre 1979; Mata and McLaughlin 1982*; Shulgin 1995*; Lundstrom

1971; Pardanini et al. 1978; Ott 1993*; Turner and Heyman 1960)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="213">Species</td>
<td valign="top" width="213">Occurrence</td>
<td valign="top" width="213">Use</td>
</tr>
<tr>
<td valign="top" width="213">Gymnocalycium gibbosum (Haw.) Pfeiffer</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Gymnocalycium leeanum (Hook.) Br. et R.</td>
<td valign="top" width="213">Argentina, Uruguay</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Islaya minor Backeb.</td>
<td valign="top" width="213">southern Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Lophophora diffusa (Croizat) Bravo</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213">peyote substitute</td>
</tr>
<tr>
<td valign="top" width="213">[syn. Lophophora echinata]</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Lophophora jourdaniana [nom. nud.]</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Lophophora williamsii (Lem.) Coult.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">[syn. Lophophora fricii Habermann]</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Myrtillocactus geometrizans (Mart.) Cons.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia acanthocarpa Engelm. et Bigel.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia basilaria Engelm. et Bigel.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia cylindrica (Lam.) S.-D.</td>
<td valign="top" width="213">Chile</td>
<td valign="top" width="213">inebriant502</td>
</tr>
<tr>
<td valign="top" width="213">Opuntia echinocarpa Engelm. et Bigel.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia ficus-indica (L.) Mill.</td>
<td valign="top" width="213">Mexico, Egypt503</td>
<td valign="top" width="213">food</td>
</tr>
<tr>
<td valign="top" width="213">Opuntia imbricata (Haw.) DC.</td>
<td valign="top" width="213">Arizona</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Opuntia spinosior (Engelm.) Tourney</td>
<td valign="top" width="213">Arizona</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pelecyphora aselliformis Ehrenb.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213">peyote substitute</td>
</tr>
<tr>
<td valign="top" width="213">Pereskia corrugata Cutak</td>
<td valign="top" width="213">Florida</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pereskia tampicana Web.</td>
<td valign="top" width="213">Mexico</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pereskiopsis scandens Br. et R.</td>
<td valign="top" width="213">Yucatan</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Polaskia chende (Gossel.) Gibs.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Polaskia sp.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pterocereus gaumeri (Br. et R.) Mac-Doug. et Mir.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Pterocereus sp.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus beneckei (Ehrenb.) Buxbaum</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus eruca (Brand.) Gibs. et Horak</td>
<td valign="top" width="213">Baja California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus stellatus (Pfeiffer) Rice</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus treleasei (Br. et R.) Backeb.</td>
<td valign="top" width="213">California</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stenocereus sp.</td>
<td valign="top" width="213"> </td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Stetsonia coryne (SD.) Br. et R.</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus bridgesii (SD.) Br. et R.</td>
<td valign="top" width="213">Peru, Bolivia</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus cuscoensis Br. et R.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus fulvinanus Ritt.</td>
<td valign="top" width="213">Chile</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus macrogonus (SD.) Ricc.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus pachanoi Br. et R.</td>
<td valign="top" width="213">Peru, Ecuador</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus peruvianus Br. et R.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213">entheogen</td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus spachianus (Lem.) Rice.</td>
<td valign="top" width="213">Indiana (cultivated)</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus strigosus (SD.) Br. et R.</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus taquimbalensis Card.</td>
<td valign="top" width="213">Peru</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus terscheckii (Parm.) Br. et R.</td>
<td valign="top" width="213">Peru, northwestern</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus validus (Monv.) Backbg.</td>
<td valign="top" width="213">Argentina</td>
<td valign="top" width="213"> </td>
</tr>
<tr>
<td valign="top" width="213">Trichocereus werdermannianus Backbg.</td>
<td valign="top" width="213">Peru, Bolivia</td>
<td valign="top" width="213"> </td>
</tr>

</table>
Commercial Forms and Regulations

Mescaline is available primarily as a hydrochloride

or sulfate. In Germany, it is considered a "narcotic in which trafficking is prohibited." In the United

States, the Controlled Substances Act lists mescaline

as a Schedule I substance (Korner 1994,38*).



Literature

See also the entries for Lophophora williamsii,

Trichocereus pachanoi, Trichocereus spp., and ~phenethylamines.

Ammon, Gunter, and Jurgen Gotte. 1971. Ergebnisse

fruher Meskalin-Forschung. In

BewuBtseinserweiternde Drogen aus

psychoanalytischer Sicht, special issue,

Dynamische Psychiatrie, 23-45.

Beringer, Kurt. 1927. Der Meskalinrausch. Berlin:

Springer. Repr. 1969.

Blofeld, John. 1966. A high yogic experience achieved

with meskalin. Psychedelic Review 7:27-32.

Doetsch, P. W., J. M. Cassidy, and J. L. McLaughlin.

1980. Cactus alkaloids. XL: Identification of

mescaline and other phenethylamines in Pereskia,

Pereskiopsis and Islaya by use of fluorescamine

conjugates. Journal ofChromotography 189:79.

Ellis, Havelock. 1971. Zum Phanomen der MeskalinIntoxikation,

Bemerkungen zum Problem der

Meskalin-Intoxikation. In

BewuBtseinserweiternde Drogen aus

psychoanalytischer Sicht, special issue,

Dynamische Psychiatrie, 17-22.

Frederking, W. 1954. Meskalin in der Psychotherapie.

Medizinischer Monatsspiegel, 3:5-7.

Harf, Jurgen C. 1996. Meskalin und Peyote. Grow!

6/96: 15-16.

Heffter, Arthur. 1894. aber zwei Kakteenalkaloide.

Berichte der deutschen Chemischen Gesellschaft

27:2975.

Kluver) Heinrich. 1926. Mescal vision and eidetic

vision. American Journal ofPsych0 logy 37:502-15.

---. 1969. Mescal and mechanisms of

hallucinations. Chicago: The University of

Chicago Press.

La Barre, Weston. 1979. Peyotl and mescaline.

Journal ofPsychedelic Drugs 11 (1-2): 33-39.

Lundstrom, Jan. 1971. Biosynthetic studies on

mescaline and related cactus alkaloids. Acta

Pharm. Suecica 8:275-302.

Michaux, Henri. 1986. Unseliges Wunder: Das

Meskalin. Munich and Vienna: Carl Hanser.

Pardanani, J. H., B. N. Meyer, and J. L. McLaughlin.

1978. Cactus alkaloids. XXXVII. Mescaline and

related compounds from Opuntia spinosior.

Lloydia 41 (3): 286-88.

Passie, Torsten. 1994. Ausrichtungen, Methoden und

Ergebnisse fruher Meskalinforschungen im

deutschsprachigen Raum (bis 1950). In Jahrbuch

des Europiiischen Collegiums fur

Bewufltseinsstudien (1993/1994), 103-11. Berlin:

VWB.

Paul., A.G., H. Rosenberg, and K. L. Khanna. 1969.

The roles of 3,4,5-trihydroxy-~-phenethylamine

and 3,4-dimethoxy-~-phenethylaminein their

biosynthesis of mescaline. Lloydia 32 (1): 36-39.

Rosenberg, H., K. L. Khanna, M. Takido, and A. G.

Paul. 1969. The biosynthesis of mescaline in

Lophophora williamsii. Lloydia 32 (3): 334-38.

Turner, W. J., and J. J. Heyman. 1960. The presence of

mescaline in Opuntia cylindrica. Journal of

Organic Chemistry 25:2250.

Wallraff, Gunter. 1968. Meskalin-Ein Selbstversuch.

Berlin: Verlag Peter-Paul Zahl.</td>
</tr>

Ibogaine

2013-01-13T18:32:38Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Endabuse, ibogain, ibogaina, ibogaIne, NIH 10567,

12-methoxy-ibogamin, 12-methoxy-ibogamine

Substance type: indole alkaloid, indole alkylamine,

ibogane type

Chemically, ibogaine is closely related to the ~carbolines,

and particularly to harmaline and

harmine. It belongs to the group of cyclic tryptamine

derivatives.

Ibogaine was first isolated from the root cortex

of Tabernanthe iboga in France in 1901 (Dybowsky

and Landgren 1901). Ibogaine and analogous

alkaloids (ibogane type) also occur in Pandaca

retusa (Lam.) Mgf. [sYll. Tabernaemontana retusa

(Lam.) Pichon] (cf. Tabernaemontana spp.), a dogbane species native to Madagscar (Le MenOlivier

et al. 1974). Many genera in the Family ApocYllaceae,

including Tabernaemontana, Voacanga

spp., Stemmadenia, Ervatamia, and Gabunea, contain

ibogaine-type indole alkaloids (ibogamine, tabernanthine,

voacangine, ibogaline) (Prins 1988, 5).

Between 1940 and 1950, most research into

ibogaine was conducted in France. Because it

exhibited potent stimulating properties, the initial

pharmacological research focused on ibogaine's

neuropharmacological effects. Only later were the

hallucinogenic effects more precisely studied

(Sanchez-Ramos and Mash 1996,357).

In the 1960s, the Chilean psychiatrist Claudio

Naranjo introduced ibogaine into psychotherapy

as a "fantasy-enhancing drug" (Naranjo 1969*).

One subject provided the following account of a

shamanic experience during a psychotherapeutic

session with the "stomach drug" ibogaine:

I am a panther! A black panther! I defend

myself, I stand up. I snort powerfully, with the

breath of a panther, predator breath! I move

like a panther, my eyes are those of a panther, I

see my whiskers. I roar) and I bite. I react like a

panther, offense is the best defense.

Now I hear drums. I dance. My joints are

gears, hinges, hubs. I can be a knee, a bolt,

could do something, indeed almost anything.

And I can loose [sic] myself again in this chaos

of nonexistence and the perception of vague,

abstract ideas of changing forms, where there

exists a sense of the truth of all things and an

order that one should set out to discover.

(Naranjo 1979, 188*)

In Europe, the Swiss psychiatrist Peter

Baumann provided the main impetus for the use

of ibogaine in psychotherapy:

Baumann reported about experiments with

completely synthetic ibogaine, which he used

on only a few patients with whom a long and

positive therapeutic relationship existed. The

dosage was usually 5 mg/kg of body weight. At

this dosage level, the effects lasted for approximately

5 to 8 hours and diminished only very

slowly. In his experiments with ibogaine, the

author found that it was not the substance as

such that triggered a specific effect but that it

induced an unspecific psychological and

physical stimulus that was then responded to

in the language that patient was accustomed

to using with this therapist. (Leuner and

Schlichting 1986, 162)

Unfortunately, an accident led to this initially

promising research being halted. Marina Prins

(1988) subsequently compared Baumann's results

with those reported by Naranjo.

Today, ibogaine is in the spotlight of

neuropharmacological research because it has

been shown that this alkaloid can be used to

reduce and cure the addictive behavior of people

dependent on other drugs (heroine, cocaine)

(Sanchez-Ramos and Mash 1996; cf. Maps 6 [2;

1996]: 4-6). For example, ibogaine has been found

to suppress the motor activity that occurs during

opiate withdrawal. It has been proposed that

ibogaine, when

ingested by opiate addicts in a single high

dosage, dramatically reduces withdrawal

symptoms while simultaneously causing a trip

that provides the patient with such deep

insights into the personal causes of the

addiction that a majority of the individuals

who receive such therapy can live for months

without relapse. However, it should be noted

that several additional sessions may be necessary before a persistent stabilization

occurs. (Naeher 1996, 12)

Experiments with primates have shown that

ibogaine reduces opiate addiction and partially

blocks withdrawal symptoms. Although the

neuropharmacological mechanism behind these

effects has not yet been discovered, Deborah Mash

and her team in Miami (Mash 1993; Mash et al.

1995) are researching this question. Ibogaine has

been demonstrated to interact with numerous

different receptors, and it has been concluded

that this breadth of interaction is the reason for

ibogaine's effectiveness in addiction therapy

(Sweetman et al. 1995).

In the United States, the use of ibogaine to treat

addiction has been patented as the clinical Lotsof

procedure (Lotsof 1995). Whether this procedure

will receive endorsement from the medical community

remains to be seen (Touchette 1995). A

novel about this facet of ibogaine (which incorporates

such actual people as Howard Lotso£) was

published in Slovenia (Knut 1994).

Ibogaine enjoys a reputation for being an

exceptionally potent and stimulating aphrodisiac

(Naranjo 1969*).500 The research to date has

entirely neglected this aspect.

Another substance of pharmacological and

therapeutic interest is noribogaine, which is

chemically and pharmacologically very similar to

Prozac (fluoxetine). In the United States, Prozac is

one of the most frequently prescribed psychopharmaca

for depression, and it is celebrated as

the "happy drug" in the popular press (Kramer

1995; Rufer 1995*).</td>
<td valign="top" width="53%">Dosage and Application

Two to four tablets containing up to 8 mg ibogaine

per tablet may be given daily as a stimulant for

states of exhaustion, debility, et cetera. Nausea,

vomiting, and ataxia are possible side effects. When

used for psychotherapeutic purposes (Baumann),

dosages of 3 to 6 mg of ibogaine hydrochloride per

kg of body weight were administered. For psychoactive

purposes, dosages of around 200 mg are

recommended (Prins 1988, 47).

Commercial Forms and Regulations

Ibogaine was formerly available as a medicine

under the trade name Bogadin (Schneider and

McArthur 1956). In the United States, ibogaine is

considered a Schedule I drug and has been

prohibited since 1970. However, ibogaine

hydrochloride is marketed under the trade name

Endabuse and can be used with the appropriate

special permit. In Germany, ibogaine is not

considered a narcotic under the guidelines of the

narcotic laws and is therefore legal (Korner 1994,

1573*).

Literature

See also the entries for Tabernaemontana spp.,

Tabernanthe iboga, Voacanga spp., and indole

alkaloids.

Baumann, Peter. 1986. "Halluzinogen"-unterstiitzte

Psychotherapie heute. Schweizerische Arztezeitung

67 (47): 2202-5.

Dybowski, J., and E. Landrin. 1901. Sur l'iboga, sur

ses proprietes excitantes, sa composition et sur

l'alcaloide nouveau qu'il renferme. Comptes

Rendues 133:748.

Fromberg, Eric. 1996. Ibogaine. Pan 3:2-8. (Includes

a very good bibliography.)

Knut, Amon Jr. 1994. Iboga. Maribor: Skupina

Zrcalo. (Cf. Curare 18 (1; 1995): 245-46.)

Kramer, Peter D. 1995. GlUck aufRezept: Der

unheimliche Erfolg der GlUckspille Fluctin.

Munich: Kosel.

Le Men-Olivier, 1., B. Richards, and Jean Le Men.

1974. Alcaloides des graines du Pandaca retusa.

Phytochemistry 13:280-81.

Lotsof, Howard S. 1995. Ibogaine in the treatment of

chemical dependence disorders: Clinical

perspectives. Maps 5 (3): 15-27.

Mash, Deborah C. 1995. Development of ibogaine as

an anti-addictive drug: A progress report from

the University of Miami School of Medicine.

Maps 6 (1): 29-30.

Mash, Deborah C., Julie K. Staley, M. H. Baumann,

R. B. Rothman, and W. 1. Hearn. 1995.

Identification of a primary metabolite of

ibogaine that targets serotonin transporters and

elevates serotonin. Life Sciences 57 (3): 45-50.

Naeher, Karl. 1996. Ibogain: Eine Droge gegen

Drogenahhangigkeit? Hanjblatt 3 (21): 12-15

(interview).

Prins, Marina. 1988. "Von Iboga zu Ibogain: Dber

eine vielseitige Droge Westafrikas und ihre

Anwendung in der Psychotherapie." Unpublished

licentiate thesis, Zurich. (Very rich bibliography.)

Sanchez-Ramos, Juan R., and Deborah Mash. 1996.

Pharmacotherapy of drug-dependence with

ibogain. Jahrbuch fur Transkulturelle Medizin und

Psychotherapie 6 (1995): 353-67.

Schneider, J., and M. McArthur. 1956. Potentiation

action of ibogain (BogadinTM) on morphin

analgesia. Experimenta 8:323-24.

Sweetman, P. M., J. Lancaster, Adele Snowman, J. 1.

Collins, S. Perschke, C. Bauer, and J. Ferkany.

1995. Receptor binding profile suggests multiple

mechanisms of action are responsible for

ibogaine's putative anti-addiction activity.

Psychopharmacology 118:369-76.

Touchette, Nancy. 1995. Anti-addiction drug ibogain

on trial. Nature Medicine 1 (4): 288-89.</td>
</tr>

</table>

5-MeO-DMT

2013-01-13T18:31:07Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Dimethyl-5-methoxytryptamine, 5-methoxy-DMT,

5-methoxy-N,N-dimethyl-tryptamine, 0-methylbufotenine,

3- [2-(dimethylamino)ethyl] -5-methoxy-

indole, toad foam

Substance type: tryptamine (indole alkaloid)

5-MeO-DMT was first discovered in Dictyoloma

incanescens DC. and later was isolated from Anadenanthera

peregrina as well. It occurs in a very

large number of plants, often in association with

N,N-DMT (see the table on pages 853-854). Its

effects are somewhat more potent than those of

N,N-DMT. When the two are administered simultaneously,

5-MeO-DMT more quickly occupies

the specific receptors. 5-MeO-DMT is a natural

neurotransmitter in the human nervous system.

When 5-MeO-DMT (10 to 20 mg) is smoked or

vaporized and inhaled, the effects are almost

immediately apparent, are incredibly extreme, and

last about ten minutes. Many people report having

shamanic experiences with this substance as well

as experiencing states of enlightenment and the

clear light of nirvana (Metzner 1988).

The Colorado River toad (Bufo alvarius) is

native to the area around Tucson, Arizona. These

toads spend nine months of the year underground,

buried in the mud that keeps them protected from

the burning desert sun. The toads emerge from

their hiding places with the first rains and begin

their courtship (Smith 1982,97-100). They remain

visible for only three months. Like all toads, Bufo

alvarius develops mucous secretions in two glands

that are located on the neck The secretions of the

Colorado River toad, however, do not contain

bufotoxine, the toxic substance that is found in the

secretions of most other toads. Instead, the dried

mass contains 15% 5-MeO-DMT (Erspamer et al.

1965, 1967).

The native tribes that lived in the North

American Southwest made fetishes of this Bufo

alvarius. However, it was only in recent times that

the toad's cultural importance and its psychedelic

use were discovered, or more likely rediscovered

(cf. Davis and Weil 1992). The toad is "milked" by

being held firmly without being crushed. Both

glands are then massaged gently until a fat stream

of the secretion squirts out. The secretion is

caught on a piece of glass, where it is allowed to

dry and crystallize. The yellowish crystalline mass

then can be scraped off, mixed with different herbs

(such as damiana [Turnera diffusa] ), and smoked.

The toad, which is released unharmed, is quickly

able to replenish the loss in its secretions.

When taken orally, Bufo alvarius secretions are

apparently toxic, whereas they are not poisonous

when smoked (Wei! and Davis 1994). Davis and

Weil have suggested that the dried secretions of

Bufo alvarius were traded to Mexico in preColumbian

times and that the priests and shamans

there smoked or used it in some other manner

(Davis and Weil1992; cf. balche', bufotenine).

In Arizona, there is now a Church of the Toad

of Light, which uses the secretions of Bufo alvarius

as a sacrament (Most 1984; Ott 1993,396*).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Pure 5-MeO-DMT is available from chemical

suppliers. While the substance is not explicitly

mentioned in the narcotics laws, the fact that it

could be interpreted as a DMT analog may result

in problems with the law.

Literature

See also the entries for bufotenine.

Davis, Wade, and Andrew T. Wei!. 1992. Identity of a

New World psychoactive toad. Ancient

Mesoamerica 3:51-59.

Erspamer, v., T. Vitali, M. Roseghini, and J. M. Cei.

1965. 5-methoxy and 5-hydroxyindolalkylamines

in the skin of Bufo alvarius.

Experientia 21:504.

---.1967. 5-methoxy- and 5-hydroxyindoles in

the skin of Bufo alvarius. Biochemical

Pharmacology 16:1149-64.

Metzner, Ralph. 1988. Hallucinogens in

contemporary North American shamanic

practice. In Proceedings ofthe Fourth

International Conference on the Study of

Shamanism and Alternate Modes ofHealing

(Independent Scholars of Asia), 170-75.

Most, A. 1984. Bufo alvarius: The psychedelic toad of

the Sonoran Desert. Denton, Texas: Venom Press.

Witsch, Christian. 1993. Die Krbtenmutter. In

Naturverehrung und Heilkunst, ed. C. R~itsch,

125-28. Sudergellersen: Bruno Martin.

Smith, Robert 1. 1982. Venomous animals ofArizona.

Bulletin 8245. Tucson: The University of Arizona.

Weil, Andrew T., and Wade Davis. 1994. Bufo

alvarius: A potent hallucinogen of animal origin.

Journal ofEthnopharmacology 41: 1-8.</td>
</tr>

</table>

Ibotenic Acid

2013-01-13T18:30:27Z

205.56.181.196:

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

a-amino (3-hydroxy-5-isoxazolyl)acetic acid, aamino-

2,3-dihydro-3-oxo-5-isoxazole-acetic acid,

ibotenic acid, «pilzatropin;' pramuscimol

Substance type: amino acid

Ibotenic acid was first isolated in 1964 from the

Japanese mushroom Amanita strobiliformis (Paul)

Quel. The Japanese name for this mushroom is ibotengu-

take ((warty tengu mushroom"), and

ibotenic acid was named after it (Ott 1993, 341*;

Takemoto et al. 1964). Ibotenic acid is also found

in Amanita muscaria and Amanita pantherina

(Eugster et al. 1965). It may also be present in

members of the genus Botelus (porcini mushrooms).

Ibotenic acid is structurally related to the

neurotransmitter glutamate and may behave

similarly in the nervous system. A psychoactive dose is regarded as 50 to 100 mg. Ibotenic acid is

converted into muscimol when stored (Good et al.

1965).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Ibotenic acid is available from chemical suppliers

and is a legal substance (Ott 1993,440*).

Literature

See also the entries for Amanita muscaria,

Amanita pantherina, and muscimol.

Eugster, C. H., G. F. R. Muller, and R. Good. 1965.

Wirkstoffe aus Amanita muscaria: Ibotensaure

und Muscazon. Tetrahedron Letters 23:1813-15.

Gagneux, A. R., et al. 1965. Synthesis of ibotenic

acid. Tetrahedron Letters 965:2081-84.

Good, R., et al. 1965. Isolierung und

Charakterisierung von Pramuscimol und

Muscazon aus Amanita muscaria (1. ex Fr.)

Hooker. Helvetica Chimica Acta 48 (4): 927-30.

Romagnesi, M. H. 1964. Champignons toxiques au

Japon. Bulletin de la Societe Mycologique de

France 80 (1): iv-v.

Takemoto, T., T. Nakajima, and R. Sakuma. 1964.

Structure of ibotenic acid. Yakugaku Zasshi

84:1233.</td>
</tr>

</table>

Ibotenic Acid

2013-01-13T18:30:17Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

a-amino (3-hydroxy-5-isoxazolyl)acetic acid, aamino-

2,3-dihydro-3-oxo-5-isoxazole-acetic acid,

ibotenic acid, «pilzatropin;' pramuscimol

Substance type: amino acid

Ibotenic acid was first isolated in 1964 from the

Japanese mushroom Amanita strobiliformis (Paul)

Quel. The Japanese name for this mushroom is ibotengu-

take ((warty tengu mushroom"), and

ibotenic acid was named after it (Ott 1993, 341*;

Takemoto et al. 1964). Ibotenic acid is also found

in Amanita muscaria and Amanita pantherina

(Eugster et al. 1965). It may also be present in

members of the genus Botelus (porcini mushrooms).

Ibotenic acid is structurally related to the

neurotransmitter glutamate and may behave

similarly in the nervous system. A psychoactive dose is regarded as 50 to 100 mg. Ibotenic acid is

converted into muscimol when stored (Good et al.

1965).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Ibotenic acid is available from chemical suppliers

and is a legal substance (Ott 1993,440*).

Literature

See also the entries for Amanita muscaria,

Amanita pantherina, and muscimol.

Eugster, C. H., G. F. R. Muller, and R. Good. 1965.

Wirkstoffe aus Amanita muscaria: Ibotensaure

und Muscazon. Tetrahedron Letters 23:1813-15.

Gagneux, A. R., et al. 1965. Synthesis of ibotenic

acid. Tetrahedron Letters 965:2081-84.

Good, R., et al. 1965. Isolierung und

Charakterisierung von Pramuscimol und

Muscazon aus Amanita muscaria (1. ex Fr.)

Hooker. Helvetica Chimica Acta 48 (4): 927-30.

Romagnesi, M. H. 1964. Champignons toxiques au

Japon. Bulletin de la Societe Mycologique de

France 80 (1): iv-v.

Takemoto, T., T. Nakajima, and R. Sakuma. 1964.

Structure of ibotenic acid. Yakugaku Zasshi

84:1233.</td>
</tr>

</table>
[gallery]

Coumarins

2013-01-13T18:28:12Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Benzopyrones, coumarine· cumarines, kumarine

Empirical formula: C9H60 2 (= 1,2-benzopyrone)

Substance type: benzopyrone

Coumarin (= chromen-2-on, kumarin, 2H-1benzopyran-

2-on, o-cumar[in] acid lactone),

which has a scent like that of vanilla, crystallizes

into colorless prisms and is easily soluble in

alcohol, ether, and essential oils. Pure coumarin is

exuded from what are known as tonka beans, and

for this reason it is also called tonka bean camphor.

Coumarin is biosynthesized by the hydroxylation

of cinnamic acid or coumarin glycoside. Even

plants that do not actually contain any coumarin often produce it when they wilt (giving off the

smell of hay) or dry (e.g., Anthoxanthum

odoratum, Galium odoratum, Sida acuta).

Coumarins in Psychoactive Plants

(from Gray and Waterman1978; Rompp 1995*; Shoeb et ai. 1973; supplemented)

Coumarins (e.g., benzofuran) have been found in the following plants with demonstrated or

purported psychoactivity:
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="319">Aegle marmelos Corr.</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Anthoxanthutn odoratumL.(sweetvernal grass)</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Dipteryx (Coumarouna) odorata (AubI.) Willd.</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Dipteryxoppositifolia (Aubl.) .Willd. (tonka bean)</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Evodia spp. (cf. Evodia bonwickii)</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Galiumodoratum(L.}Scop.(woodruff) [syn. Asperula odorata 1.]</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Hierochloe australis (1.) P. Beauv. (buffalo grass; vodka additive)</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Flierochloe odorata (L.) P. Beauv. (sweet grass, vanilla grass; cf. incense)</td>
<td valign="top" width="319">unidentified</td>
</tr>
<tr>
<td valign="top" width="319">Justicia pectoralis</td>
<td valign="top" width="319">coumarin and others</td>
</tr>
<tr>
<td valign="top" width="319">Laval1dula angustifolia Mill. [syn. Lavandula officinalis Chaix] (c£ essential oils)</td>
<td valign="top" width="319">coumarin and others</td>
</tr>
<tr>
<td valign="top" width="319">Melilotus officinalis (1.) Pall.</td>
<td valign="top" width="319">various</td>
</tr>
<tr>
<td valign="top" width="319">Melilotus spp. (sweet clover)</td>
<td valign="top" width="319">furanocoumarins</td>
</tr>
<tr>
<td valign="top" width="319">Petroselinum crispum</td>
<td valign="top" width="319">rutin, gravolenic

acid</td>
</tr>
<tr>
<td valign="top" width="319">Rutagraveolens 1. (cf. haoma, soma)</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Sida acuta</td>
<td valign="top" width="319">coumarin</td>
</tr>
<tr>
<td valign="top" width="319">Sidaspp.</td>
<td valign="top" width="319">various</td>
</tr>
<tr>
<td valign="top" width="319">Tagetes spp.</td>
<td valign="top" width="319">various</td>
</tr>
<tr>
<td valign="top" width="319">Thamnosma montana</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">For plants containing the coumarin derivative scopoletin, see scopoletin.</td>
<td valign="top" width="319"> </td>
</tr>

</table>
Umbelliferone, aesculine, and furocoumarin

are all coumarin derivatives. More than six

hundred natural coumarins are now known.

About two hundred coumarins occur in the

Family Rutaceae (including the genera Zanthoxylum,

Evodia, Ruta, Thamnosma, Dictamnus, Eriostemon,

Citrus, and Aegle), where they appear to

have great chemotaxonomic importance (Gray and

Waterman 1978; Tatum and Berry 1979).

Coumarins occur in some plants that are used

for psychoactive purposes (see scopoletin). Coumarin

is the substance responsible for the specific

taste of woodruff punch, and it is also present in

fahan tea (Angraecum fragrans Du Petit-Thouars),

which Bibra (1855*) described as psychoactive.

Fahan was once used as a substitute for green tea

(Camellia sinensis) and was mixed with tobacco

(Nicotiana tabacum) and rolled into cigars

(Frerichs et al. 1938, 1234*).

High dosages of pure coumarin can cause

headaches, dizziness, lethargy, stupor, and even

respiratory paralysis (Roth et al. 1994, 796*).

Coumarin is said to be toxic to the liver and for

this reason was banned as a component or

ingredient in food. However, the toxicity is very

doubtful, and the alleged carcinogenic effects are

also questionable (Marles et al. 1987).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

In the United States, coumarin has been banned as

a food additive since 1954. It has been placed in Class 3 of the Swiss Poison List. In Germany,

drinking brandies (380/0 alcohol) are allowed to

contain a maximum of 10 mg of coumarin per

liter (Roth et al. 1994,402*).

Literature

See also the entries for scopoletin.

Gray, Alexander 1., and Peter Waterman. 1978.

Coumarins in the Rutaceae. Phytochemistry

17:845-64. (Contains a rich bibliography.)

Marles, R. J., C. M. Compadre, and N. R. Farnsworth.

1987. Coumarin in vanilla extracts: Its detection

and significance. Economic Botany 41 :41-47.

Mendez, R. D. H., J. Murray, and S. A. Brown. 1982.

The natural coumarins. Chichester, U.K.: John

Wiley.

Reisch, J., et al. 1968. Dber weitere C3-substituierte

Cumarin-Derivate aus Ruta graveolens:

Daphnoretin und Daphnoretin-methyHither.

Planta Medica 15:372-76.

---. 1969. Dber die Cumarine der Wurzel von

Ruta graveolens. Planta Medica 17:116-19.

Shoeb, Aboo, Rhandhir S. Kapil, and Satya P. PopIi.

1973. Coumarins and alkaloids of Aegle

marmelos. Phytochemistry 12:2071-72.

Tatum, James H., and Robert E. Berry. 1979.

Coumarins and psoralkens in grapefruit peel oil.

Phytochemistry 18:500-502.</td>
</tr>

</table>

Diterpenes

2013-01-13T18:27:25Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Diterpene, diterpenes, diterpenoids, diterpenos

Diterpenes are not alkaloids but non-nitrogenous

natural substances composed of four isoprene

groups. They are related to the monoterpenes and

sesquiterpenes and belong to the terpene group.

Diterpenes occur in numerous plants and several

essential oils.

Some diterpenes regulate plant growth. Termites,

sponges (Spongia spongens 1.), and coelenterates

contain bioactive diterpenes that have

inhibiting effects upon certain bacteria (Buchbauer

et al. 1990, 28). There are even sweet-tasting

diterpenes, such as the natural sweetening agents

in Stevia rebaudiana (Bert.) Hemsl., the leaves of

which are used to sweeten mate (cf. Ilex

paraguariensis) .

The first psychoactive diterpene to be

discovered was salvinorin A. It is very likely that

there are other psychoactive diterpenes that have not yet been isolated, pharmacologically tested, or

chemically described. Some psychoactive alkaloids

are diterpene derivatives. Aconitine, the primary

active constituent in monkshood (cf. Aconitum

ferox, Aconitum napellus), is a diterpene alkaloid.

Diterpene alkaloids also occur in Delphinium and

Spiraea.</td>
<td valign="top" width="53%"> Diterpenes in Psychoactive Plants

(from Buchbauer et al. 1990; Rein 1979; supplemented)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="319">Stock Plant</td>
<td valign="top" width="319">Distribution</td>
</tr>
<tr>
<td valign="top" width="319">Coleus blumei</td>
<td valign="top" width="319">bicyclic diterpenes</td>
</tr>
<tr>
<td valign="top" width="319">Coleus spp.</td>
<td valign="top" width="319">forskolin, labdanes, coleones</td>
</tr>
<tr>
<td valign="top" width="319">Crocus sativus</td>
<td valign="top" width="319">crocetine (as glycoside)</td>
</tr>
<tr>
<td valign="top" width="319">Helichrysum spp. (cf. Helichrysum foetidum)</td>
<td valign="top" width="319">various</td>
</tr>
<tr>
<td valign="top" width="319">Jatropha grossidentata</td>
<td valign="top" width="319">jatrophone</td>
</tr>
<tr>
<td valign="top" width="319">Lagochilus inebrians</td>
<td valign="top" width="319">lagochiline (diterpene alcohol)</td>
</tr>
<tr>
<td valign="top" width="319">Leonotis leonurus</td>
<td valign="top" width="319">various</td>
</tr>
<tr>
<td valign="top" width="319">Leonurus sibiricus</td>
<td valign="top" width="319">various</td>
</tr>
<tr>
<td valign="top" width="319">Nicotiana sylvestris Spegazz.</td>
<td valign="top" width="319">2,7, Il-duvatrien-4,6-diol</td>
</tr>
<tr>
<td valign="top" width="319">Nicotiana tabacum</td>
<td valign="top" width="319">labdanes or duvanes</td>
</tr>
<tr>
<td valign="top" width="319">Nicotiana tomentosiformis Goodspeed</td>
<td valign="top" width="319">labdanes</td>
</tr>
<tr>
<td valign="top" width="319">Nicotiana spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Petunia patagonica (Spegazz.) Millan</td>
<td valign="top" width="319">various</td>
</tr>
<tr>
<td valign="top" width="319">(cf. Petunia violacea)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Piper auritum</td>
<td valign="top" width="319">trans-phytol</td>
</tr>
<tr>
<td valign="top" width="319">Salvia divinorum</td>
<td valign="top" width="319">salvinorin A, salvinorin B (clerodanes)</td>
</tr>
<tr>
<td valign="top" width="319">Scoparia dulcis</td>
<td valign="top" width="319">labdanediterpenes</td>
</tr>
<tr>
<td valign="top" width="319">Taxus baccata 1. (cf. witches' ointments)</td>
<td valign="top" width="319">taxines, taxol</td>
</tr>
<tr>
<td valign="top" width="319">Taxus brevifolia Nutt.</td>
<td valign="top" width="319">taxines</td>
</tr>
<tr>
<td valign="top" width="319">Taxus canadensis Marsh.</td>
<td valign="top" width="319">taxines</td>
</tr>
<tr>
<td valign="top" width="319">Taxus cuspidata Sieb. et Zucco</td>
<td valign="top" width="319">taxines</td>
</tr>
<tr>
<td valign="top" width="319">Taxus wallichiana</td>
<td valign="top" width="319">taxines</td>
</tr>

</table>
Literature

See also the entries for Coleus blumei, Salvia

divinorum, and salvinorin A.

Buchbauer, Gerhard, Helmut Spreizer, and Gabriele

Kiener. 1991. Biologische Wirkungen von

Diterpenen. Pharmazie in unserer Zeit 19 (1):

28-37.

Reid, W. W. 1979. The diterpenes of the Nicotiana

species and N. tabacum cultivars. In The biology

and taxonomy of the Solanaceae, ed. J. G. Hawkes,

R. N. Lester, and A. Skelding, 273-78. London:

Academic Press.</td>
</tr>

</table>

Diazepam

2013-01-13T18:26:16Z

205.56.181.196:

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

7-chlor-1,3-dihydro-1-methyl-5-phenyl-2H-1,4benzodiazepin-

2-on, sleeping pill, tranquilizer,

Valium

Substance type: benzodiazepine

Diazepam, better known as Valium, was originally

synthesized in the laboratory and introduced as a

therapeutic drug (psychopharmaca, tranquilizer)

in the 1960s. The substance produces sedative,

euphoric, and especially anxiolytic (anxietyreducing)

effects (Henningfield 1988, 17,35*).

During the investigation of diazepam's

pharmacology, it was discovered that the human

nervous system has a special receptor for this

molecule, known as the benzodiazepine receptor

or the [3H] -diazepam receptor. Luk et al. (1983)

found three isoflans in the urine of cattle that may

possibly dock (as neurotransmitters) in the

benzodiazepine receptor. It is known that the

kavapyrones (cf. Piper methysticum) bind to the

[3H] -diazepam receptor. Recently, flavonoids in

the buds of the South American linden tree (Tilia

tomentosa Moench; Tiliaceae; cf. tila) were found

to bind to the benzodiazepine receptor. A

substance found in Passiflora caerulea 1. (cf.

Passiflora spp.), 5,7-dihydroxyflavone, also docks

to the same location (Viola et al. 1994).

The benzodiazepine receptor has been shown

to be present in all vertebrates, suggesting that it

appeared at a very early date in the evolution of

the nervous system and has been preserved into

the present. This indicates that it plays an

important function in the nervous system and that

there are endogenous substances that bind to it in

order to transmit certain messages (Muller 1988).

But what do these substances look like? At first

they were thought to be polypeptides, but then

traces of diazepam and desmethyldiazepam were

discovered in the brains of humans and other

animals. Because diazepam and its initial

metabolite appear in breast milk and the placenta

after the ingestion of Valium (Wessen et al. 1985),

it was first believed that the diazepam must have

been introduced into the body from outside" But

when diazepam was subsequently also found to be

present in brains that dated to a time before the

discovery of Valium synthesis, it was concluded

that diazepam was not a synthetic chemical at all

but a naturally occurring neurotransmitter in the

nervous system (Muller 1988). Thus it was

demonstrated that "Valium, the very symbol of

chemical psychopharmaca" (Zehentauer 1992,

121 *), is actually a natural substance.

Pharmacologists were surprised when subsequent

research demonstrated the presence of diazepam

and desmethyldiazepam in potatoes (Solanum

tuberosum 1.; cf. Solanum spp.) and in such diverse

grains as wheat (Triticum aestivum 1.; cf. beer),

corn/maize (Zea mays), and rice (Oryza sativa 1.;

cf. sake) (Muller 1988). Valium, in other words, is

a natural active constituent in plants. However, the

concentration in these plants is so low that a

person would likely not notice any Valium effects

even after consuming a whole sack of potatoes.

Valium is one of the most widely used sedative

drugs in modern society and is normally prescribed

for the treatment of anxiety and sleeping

disorders.498 Not surprisingly, Valium also finds

use as a recreational drug in some circles, particularly

in combination with other substances. Its

euphoric properties can be greatly affected by

alcohol, which can at times counteract the sedative

properties, resulting in powerful stimulating effects.

Valium is one of the more commonly used

psychopharmaca in the music scene. Several rock

bands, including the classic "space rock" band

Hawkwind CValium 10," 1978), have dedicated

titles to the substance.</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Valium is available by prescription only. In the

United States, it is listed as a Schedule IV drug

under the Controlled Substances Act.

'''Literature'''

Flesch, Peter. 1996. SchlafstOrungen bei iilteren

Patienten: Auf Benzodiazepine kann meist

verzichtet werden. Jatros Neurologie 12:6-7

(interview).

Henningsfield, Jack E. 1988. Barbiturates: Sleeping

potion or intoxicant. The Encyclopedia of

Psychoactive Drugs. London, Toronto, and New

York: Burke Publishing Company.

Luk, Kin-Chun, Lorraine Stern, Manfred Weigele,

Robert A. O'Brien, and Nena Sprit. 1983.

Isolation and identification of "diazepam-like"

compounds from bovine urine. Journal of

Natural Products 46 (6): 852-61.

Muller, Walter E. 1988. Sind Benzodiazipine 100%

Natur? Deutsche Apotheker Zeitung126 (13): 672-74.

Viola, H., C. Wolfman, M. Levi de Stein, C.

Wasowski, C. Pena, J. H. Medina, and A. C.

Paladini. 1994. Isolation of pharmacologically

active benzodiazepine receptor ligands from Tilia

tomentosa (Tiliaceae). Journal of

Psychopharmacology 44:47-53.

Wesson, Donald R, Susan Camber, Martha Harkey,

and David E. Smith. 1985. Diazepam and

desmethyldiazepam in breast milk. Journal of

Psychoactive Drugs 17 (1): 55-56.</td>
</tr>

</table>

Diazepam

2013-01-13T18:25:17Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

7-chlor-1,3-dihydro-1-methyl-5-phenyl-2H-1,4benzodiazepin-

2-on, sleeping pill, tranquilizer,

Valium

Substance type: benzodiazepine

Diazepam, better known as Valium, was originally

synthesized in the laboratory and introduced as a

therapeutic drug (psychopharmaca, tranquilizer)

in the 1960s. The substance produces sedative,

euphoric, and especially anxiolytic (anxietyreducing)

effects (Henningfield 1988, 17,35*).

During the investigation of diazepam's

pharmacology, it was discovered that the human

nervous system has a special receptor for this

molecule, known as the benzodiazepine receptor

or the [3H] -diazepam receptor. Luk et al. (1983)

found three isoflans in the urine of cattle that may

possibly dock (as neurotransmitters) in the

benzodiazepine receptor. It is known that the

kavapyrones (cf. Piper methysticum) bind to the

[3H] -diazepam receptor. Recently, flavonoids in

the buds of the South American linden tree (Tilia

tomentosa Moench; Tiliaceae; cf. tila) were found

to bind to the benzodiazepine receptor. A

substance found in Passiflora caerulea 1. (cf.

Passiflora spp.), 5,7-dihydroxyflavone, also docks

to the same location (Viola et al. 1994).

The benzodiazepine receptor has been shown

to be present in all vertebrates, suggesting that it

appeared at a very early date in the evolution of

the nervous system and has been preserved into

the present. This indicates that it plays an

important function in the nervous system and that

there are endogenous substances that bind to it in

order to transmit certain messages (Muller 1988).

But what do these substances look like? At first

they were thought to be polypeptides, but then

traces of diazepam and desmethyldiazepam were

discovered in the brains of humans and other

animals. Because diazepam and its initial

metabolite appear in breast milk and the placenta

after the ingestion of Valium (Wessen et al. 1985),

it was first believed that the diazepam must have

been introduced into the body from outside" But

when diazepam was subsequently also found to be

present in brains that dated to a time before the

discovery of Valium synthesis, it was concluded

that diazepam was not a synthetic chemical at all

but a naturally occurring neurotransmitter in the

nervous system (Muller 1988). Thus it was

demonstrated that "Valium, the very symbol of

chemical psychopharmaca" (Zehentauer 1992,

121 *), is actually a natural substance.

Pharmacologists were surprised when subsequent

research demonstrated the presence of diazepam

and desmethyldiazepam in potatoes (Solanum

tuberosum 1.; cf. Solanum spp.) and in such diverse

grains as wheat (Triticum aestivum 1.; cf. beer),

corn/maize (Zea mays), and rice (Oryza sativa 1.;

cf. sake) (Muller 1988). Valium, in other words, is

a natural active constituent in plants. However, the

concentration in these plants is so low that a

person would likely not notice any Valium effects

even after consuming a whole sack of potatoes.

Valium is one of the most widely used sedative

drugs in modern society and is normally prescribed

for the treatment of anxiety and sleeping

disorders.498 Not surprisingly, Valium also finds

use as a recreational drug in some circles, particularly

in combination with other substances. Its

euphoric properties can be greatly affected by

alcohol, which can at times counteract the sedative

properties, resulting in powerful stimulating effects.

Valium is one of the more commonly used

psychopharmaca in the music scene. Several rock

bands, including the classic "space rock" band

Hawkwind CValium 10," 1978), have dedicated

titles to the substance.</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Valium is available by prescription only. In the

United States, it is listed as a Schedule IV drug

under the Controlled Substances Act.

Literature

Flesch, Peter. 1996. SchlafstOrungen bei iilteren

Patienten: Auf Benzodiazepine kann meist

verzichtet werden. Jatros Neurologie 12:6-7

(interview).

Henningsfield, Jack E. 1988. Barbiturates: Sleeping

potion or intoxicant. The Encyclopedia of

Psychoactive Drugs. London, Toronto, and New

York: Burke Publishing Company.

Luk, Kin-Chun, Lorraine Stern, Manfred Weigele,

Robert A. O'Brien, and Nena Sprit. 1983.

Isolation and identification of "diazepam-like"

compounds from bovine urine. Journal of

Natural Products 46 (6): 852-61.

Muller, Walter E. 1988. Sind Benzodiazipine 100%

Natur? Deutsche Apotheker Zeitung126 (13): 672-74.

Viola, H., C. Wolfman, M. Levi de Stein, C.

Wasowski, C. Pena, J. H. Medina, and A. C.

Paladini. 1994. Isolation of pharmacologically

active benzodiazepine receptor ligands from Tilia

tomentosa (Tiliaceae). Journal of

Psychopharmacology 44:47-53.

Wesson, Donald R, Susan Camber, Martha Harkey,

and David E. Smith. 1985. Diazepam and

desmethyldiazepam in breast milk. Journal of

Psychoactive Drugs 17 (1): 55-56.</td>
</tr>

</table>

Cytisine

2013-01-13T18:24:14Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Baptitoxin, CYtiton, laburnin, 1,2,3,4,5,6-hexahydro8H-

1,5-methano-pyrido[1,2a] [1,5]diazocin-8-ol,

sophorin, ulexin

Substance type: quinolizidine alkaloid, lupine

alkaloid

Cytisine is found in numerous legumes (Leguminosae)

(Plugge 1895), such as the rain shower

tree (Laburnum anagyroides Medikus [syn. Cytisus

laburnum 1.] ).497

Since cytisine acts to stimulate the central

nervous system, states of excitation and

confusion (with hallucinations, delirium),

muscle spasms, as well as general clonic-tonic

spasms in the extremities not infrequently

occur. (Roth et al. 1994,443*)

Cytisine docks to the acetylcholine (ACh)

receptors of the central nervous system, the

ganglia, and the neuromuscular endplate. The

ganglia-blocking effects of cytisine are similar to

those of nicotine and can induce strychninelike

spasms, especially hallucinations, and even

unconsciousness and ultimately death. However,

the lethal dosage for humans is unknown (Roth et

al. 1994, 801 f. *). The nicotine-like effects also

explain the ethnopharmacological use of plants

containing cytisine as tobacco substitutes.

Other lupine alkaloids and cytisine derivatives

have been found in many plants from the Family

Leguminosae, including Lupinus spp. and Echinosophora

koreensis Nakai (a close relative of the

genus Sophora) (Murakoshi et al. 1977).

Plants Containing Cytisine

(from Bock 1994,75 ff.*; Rompp 1995*; Roth et al. 1994*; supplemented)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="319">Stock Plant</td>
<td valign="top" width="319">Distribution</td>
</tr>
<tr>
<td valign="top" width="319">Ammodendron spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Anagyris spp.</td>
<td valign="top" width="319">southern Europe</td>
</tr>
<tr>
<td valign="top" width="319">Baptisia spp.</td>
<td valign="top" width="319">North America</td>
</tr>
<tr>
<td valign="top" width="319">Colutea.arborescens 1.</td>
<td valign="top" width="319">Mediterranean region</td>
</tr>
<tr>
<td valign="top" width="319">Calutea spp.</td>
<td valign="top" width="319">southeastern Europe, Asia Minor</td>
</tr>
<tr>
<td valign="top" width="319">Cytisus canariensis</td>
<td valign="top" width="319">Canary Islands, Mexico</td>
</tr>
<tr>
<td valign="top" width="319">Cytisus spp.</td>
<td valign="top" width="319">Europe</td>
</tr>
<tr>
<td valign="top" width="319">Eucresta spp.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Genista germanica 1.</td>
<td valign="top" width="319">central Europe</td>
</tr>
<tr>
<td valign="top" width="319">Genista tinctoria 1.</td>
<td valign="top" width="319">Europe</td>
</tr>
<tr>
<td valign="top" width="319">Labttrnum alpinum (Mill.) Bercht.et Presl</td>
<td valign="top" width="319">Alps, southern Europe</td>
</tr>
<tr>
<td valign="top" width="319">[syn. Cytisus alpinusMill.]</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Laburnum anagyroides Medik. [syn. Laburnum vulgare</td>
<td valign="top" width="319">central and southern Europe</td>
</tr>
<tr>
<td valign="top" width="319">Bercht.et Pres!' Cytisus laburnum 1.]</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Lamprolobium fruticosumBenth.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Lampralobium grandiflorum Everist</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Hovea acutifalia Cunn.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Hoveaspp.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Plagiocarpus axiUaris Benth.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Sophora secundiflora</td>
<td valign="top" width="319">Mexico, Texas</td>
</tr>
<tr>
<td valign="top" width="319">Sophora tomentosa 1.</td>
<td valign="top" width="319">Australia, Oceania</td>
</tr>
<tr>
<td valign="top" width="319">Spartium junceum 1.</td>
<td valign="top" width="319">Spain, southern Europe</td>
</tr>
<tr>
<td valign="top" width="319">Strongylodon macrobotrys A.Gray</td>
<td valign="top" width="319">Philippines</td>
</tr>
<tr>
<td valign="top" width="319">Templetonia spp.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Thel'mopsis spp.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319">Ulex europaeus 1.</td>
<td valign="top" width="319">central Europe</td>
</tr>

</table>
 </td>
<td valign="top" width="53%">Commercial Forms and Regulations

Cytisine is sold in its pure form and is not subject

to any regulations (Roth et al. 1994, 802).

Literature

See also the entries for Cytisus spp. and Sophora

secundiflora.

Hayman, Alison R., and David O. Gray. 1989.

Hydroxynorcytisine, a quinolizidine alkaloid

from Laburnum anagyroides. Phytochemistry 28

(2): 673-75.

Murakoshi, Isamu, Kyoko Fukuchi, Joju Haginiwa,

Shigeru Ohmiya, and Hirotaka Otomasu. 1977.

N-(3-oxobutyl)cytisine: A new lupin alkaloid from Echinosophora koreensis. Phytochemistry

16:1460-6l.

Plugge, P. C. 1895. Uber das Vorkommen von Cytisin

in verschiedenen Papilionaceae. Archiv fur

Pharmazie 233:430 ff.

Plugge, P. C., and A. Rauwerda. 1896. Fortgesetzte

Untersuchungen Dber das Vorkommen von

Cytisin in verschiedenen Papilionaceae. Archiv

fur Pharmazie 234:685 ff.

Seeger, R., and H. G. Neumann. 1992. Cytisin.

Deutsche Apotheker Zeitung 132:303-6.</td>
</tr>

</table>

Salvinorin A

2013-01-13T18:23:08Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

DivinorinA

Substance type: diterpene (derodane)

Salvinorin A is the active constituent in Salvia

divinorum. Apart from THe and the constituents

in essential oils, it is the only known nonnitrogenous

psychoactive plant constituent.

Salvinorin is not an alkaloid.

The substance was first described by Ortega et

al., who named it salvinorin (1982). The same

substance was subsequently described under the

name divinorin A (Valdes et al. 1984). Salvinorin

A is extracted from fresh plant material. The

effective dosage is between 200 and 500 /-Lg.

Salvinorin A can be smoked in a glass pipe; a

better technique involves vaporizing the plant and

then inhaling the fumes. It can also be taken in

solution under the tongue. When the substance is

smoked or inhaled, the effects are immediately

apparent, and the primary effects last from five to

ten minutes. When it is administered sublingually,

the effects become manifest after about ninety

seconds and reach their peak some ten to fifteen

minutes later, after which they gradually diminish

(Turner 1996).

The potent and strange psychoactive effects of

salvinorin A were probably discovered by Daniel

Siebert:

Salvinorin A is an extremely powerful compound

for altering consciousness. In fact, it is

the most potent naturally occurring hallucinogen

that has been isolated to date. But

before potential experimenters become too

interested, it must be clearly stated that the

effects are often extremely unnerving and that

there is a very real risk that persons may

physically harm themselves when using it....

I have seen people get up and jump across

the room, thereby falling over the furniture,

babbling incomprehensible nonsense, and

hitting their heads against the wall. Several

people tried to leave the house. When the

experience was over, they did not remember what had happened. In fact, they actually

believed that they remembered entirely different

events. To an outside observer, it appears

as though these people have an emptyexpression

in their eyes, as though they are not

present (and perhaps they really are not).

(Siebert 1995,4)

This description is strongly remInIscent of

phenomena that occur with high dosages (overdoses)

of nightshades (Atropa belladonna, Brugmansia

spp., Hyoscyamus niger, Datura spp.) and

the tropane alkaloids atropine and scopolamine.

Most subjects have no desire at all to repeat an

experiment with salvinorin.

The neurochemistry of salvinorin A is still

unresolved. In spite of extensive receptor testing

(NovaScreen method), salvinorin A has not been

found to bind to any known neurotransmitter

receptors, including the receptor that ketamine

occupies (David Nichols, pers. comm.). The daring

and extreme experiments of D. M. Turner suggest

that salvinorin A does not have any negative crosstolerance

with other psychoactive substances (such

as LSD, N,N-DMT, ketamine) (Turner 1996).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

None

Literature

See also the entries for Coleus blumei, Salvia divinorum,

and diterpenes.

Ortega, A., J. F. Blount, and P. S. Marchand. 1982.

Salvinorin, a new trans-neoclerodane diterpene

from Salvia divinorum (Labiatae). Journal ofthe

Chemical Society, Perkin Transactions 1:2505-8.

Siebert, Daniel J. 1995. Salvinorin A: Vorsicht

geboten. Entheogene 3:4-5.

Turner, D. M. 1996. Salvinorin: The psychedelic

essence ofSalvia divinorum. San Francisco:

Panther Press.

Valdes, Leander, William M. Butler, George M.

Hatfield, Ara G. Paul, and Masato Koreeda. 1984.

Divinorin A, a psychotropic terpenoid, and

divinorin Bfrom the hallucinogenic Mexican

mint Salvia divinorum. Journal ofOrganic

Chemistry 49 (24): 4716-20.</td>
</tr>

</table>

Yohimbine

2013-01-13T18:22:02Z

205.56.181.196:

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Aphrodin, corymbin, corynin, hydroergotocin,

johimbin, quebrachin, quebrachina, yohimbenin,

N yohimbin, yohimbina, yohimbinum, yohimvetol Substance type: aspidosperma alkaloid, indole

alkaloid

Yohimbine was first extracted from the bark of Pausinystalia yohimba and described in the

nineteenth century. It is a typical alkaloid in plants

from the Apocynaceae Family and is related to the

Rauvolfia alkaloids, and it constitutes the primary

alkaloid (1 0/0) in Alstonia angustifolia. It is also

present in some species of Rauvolfia, especially the

African species Rauvolfia macrophylla Stapf

(Timmins and Court 1974).

Yohimbine was once regarded as an MAO

inhibitor, a view that is no longer considered accurate.

Rather, it is simply an a -adrenergic blocker

that consequently stimulates the release of noradrenaline

at the nerve endings. This makes

noradrenaline available in the corpus cavernosum

and results in an erection (Roth et al. 1994, 955*;

Wren 1988,292*).

As a sympathicolytic agent, [yohimbine]

dilates the peripheral blood vessels and

reduces blood pressure. The aphrodisiac effect

is explained through a vasodilatation of the

genital organs and an increased excitability of

the reflexes in the sacral medulla. (Roth et al.

1994,545*)

Yohimbine's aphrodisiac and virility-enhancing

effects, and its therapeutic efficaciousness in

treating impotence, have been demonstrated in a

number of clinical double-blind studies (Buffum

1982; Miller 1968; Sobotka 1969).505

Consequently, yohimbine hydrochloride has

been approved as a specific medicine for the treatment of impotence (sexual neurasthenia). The

recommended dosage is 5 to 10 mg taken three

times daily as a short-term treatment over three to

four weeks. Higher individual dosages (15 to 25

mg) result in psychoactive effects that are somewhat

reminiscent of those of LSD, but with much

less emotional content and an emphasis on

physical phenomena (sexual desire, erotic enjoyment,

and increased sensations of pleasure).

Overdoses can be unpleasant but do not appear to be particularly dangerous (cf. Lewin 1992, 750*):

A chemist had taken an almost 1000-fold

dosage (1.8 g). He became unconscious for a

few hours (during which time a pronounced

priapism was observed) but was able to be

discharged from the hospital within a day.

(Roth et al. 1994,956*)

Commercial Forms and Regulations

The alkaloid is available as yohimbine hydrochloride.

Yohimbine is a prescription medication.</td>
<td valign="top" width="53%">Plants ContainingYohimbine

(from Geschwinde 1996, ·145 f. *; Hofmann

1954;Lewin 1992*; Rompp 1995,5093*; Roth

et al. 1994*; supplemented)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="319">Stock Plant</td>
<td valign="top" width="319">Distribution</td>
</tr>
<tr>
<td valign="top" width="319">Alstonia spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Alstonia angustifolia</td>
<td valign="top" width="319">Old World</td>
</tr>
<tr>
<td valign="top" width="319">Alstonia scholaris</td>
<td valign="top" width="319">Southeast Asia</td>
</tr>
<tr>
<td valign="top" width="319">Aspidosperma</td>
<td valign="top" width="319">South America</td>
</tr>
<tr>
<td valign="top" width="319">quebracho-blanco</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Catharanthus lanceus</td>
<td valign="top" width="319">North America</td>
</tr>
<tr>
<td valign="top" width="319">Corynanthe spp.</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">Mitragyna stipulosa</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">(cf.palm wine)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Pausinystalia yohimba</td>
<td valign="top" width="319">West Africa</td>
</tr>
<tr>
<td valign="top" width="319">Pausirtystalia· macroceras</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Pausinystaliatrillesii</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia macrophylla</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">Stapf</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia serpentina</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Benth.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia volkensii</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">Vincaspp.</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">(cf. Catharanthus roseus)</td>
<td valign="top" width="319"> </td>
</tr>

</table>
Literature

See also the entries for Alstonia scholaris, Corynanthe

spp., and Pausinystalia yohimba.

Buffum, John. 1982. Pharmacosexology: The effects

of drugs on sexual function-a review. Journal of

Psychoactive Drugs 14 (1-2): 5-44.

Finch, N., and W. I. Taylor. 1962. Oxidative

transformation of indole alkaloids. 1:

Preparation of oxindoles from yohimbine.

Journal of the American Chemical Society

84:3871-77.

Hofmann, Albert. 1954. Die Isolierung weiterer

Alkaloide aus Rauwolfia serpentina Benth.

Helvetica Chimica Acta 37:849-65.

Lambert, G. A., W. J. Lang, E. Friedman, E. Meller,

and S. Gershon. 1978. Pharmacological and

biological properties of isomeric yohimbine

alkaloids. European Journal ofPharmacology

49:39-48.

Leary, Timothy. 1985. Auf der Suche nach dem

wahren Aphrodisiakum und e1ektronischer Sex.

Sphinx Magazin 35.

Miller, W. W. 1968. Afrodex in the treatment of male

impotence: A double-blind cross-over study.

Current Therapeutic Research 10:354-59.

Poisson, J. 1964. Recherches recentes sur les

alcaloYdes du pseudocinchona et du yohimbine.

Ann. Chim. 9:99-121.

Porst, H. 1996. Orale und intracavernose

Pharmakotherapie. TW Urologie Nephrologie 8

(2): 88-94.

Sobotka, J. J. 1969. An evaluation of Afrodex in the

management of male impotency: A double-blind

cross-over study. Current Therapeutic Research

11:87-94.

Timmins, Peter, and William E. Court. 1974.

Alkaloids of Rauwolfia macrophylla.

Phytochemistry 13:281-82.

Weyers, Wolfgang. 1982. Die Empfehlung in der

Selbstmedikation. Heusenstamm: Keppler Verlag.</td>
</tr>

</table>

Yohimbine

2013-01-13T18:20:52Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Aphrodin, corymbin, corynin, hydroergotocin,

johimbin, quebrachin, quebrachina, yohimbenin,

N yohimbin, yohimbina, yohimbinum, yohimvetol Substance type: aspidosperma alkaloid, indole

alkaloid

Yohimbine was first extracted from the bark of Pausinystalia yohimba and described in the

nineteenth century. It is a typical alkaloid in plants

from the Apocynaceae Family and is related to the

Rauvolfia alkaloids, and it constitutes the primary

alkaloid (1 0/0) in Alstonia angustifolia. It is also

present in some species of Rauvolfia, especially the

African species Rauvolfia macrophylla Stapf

(Timmins and Court 1974).

Yohimbine was once regarded as an MAO

inhibitor, a view that is no longer considered accurate.

Rather, it is simply an a -adrenergic blocker

that consequently stimulates the release of noradrenaline

at the nerve endings. This makes

noradrenaline available in the corpus cavernosum

and results in an erection (Roth et al. 1994, 955*;

Wren 1988,292*).

As a sympathicolytic agent, [yohimbine]

dilates the peripheral blood vessels and

reduces blood pressure. The aphrodisiac effect

is explained through a vasodilatation of the

genital organs and an increased excitability of

the reflexes in the sacral medulla. (Roth et al.

1994,545*)

Yohimbine's aphrodisiac and virility-enhancing

effects, and its therapeutic efficaciousness in

treating impotence, have been demonstrated in a

number of clinical double-blind studies (Buffum

1982; Miller 1968; Sobotka 1969).505

Consequently, yohimbine hydrochloride has

been approved as a specific medicine for the treatment of impotence (sexual neurasthenia). The

recommended dosage is 5 to 10 mg taken three

times daily as a short-term treatment over three to

four weeks. Higher individual dosages (15 to 25

mg) result in psychoactive effects that are somewhat

reminiscent of those of LSD, but with much

less emotional content and an emphasis on

physical phenomena (sexual desire, erotic enjoyment,

and increased sensations of pleasure).

Overdoses can be unpleasant but do not appear to be particularly dangerous (cf. Lewin 1992, 750*):

A chemist had taken an almost 1000-fold

dosage (1.8 g). He became unconscious for a

few hours (during which time a pronounced

priapism was observed) but was able to be

discharged from the hospital within a day.

(Roth et al. 1994,956*)

Commercial Forms and Regulations

The alkaloid is available as yohimbine hydrochloride.

Yohimbine is a prescription medication.</td>
<td valign="top" width="53%">Plants ContainingYohimbine

(from Geschwinde 1996, ·145 f. *; Hofmann

1954;Lewin 1992*; Rompp 1995,5093*; Roth

et al. 1994*; supplemented)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">
<tbody>
<tr>
<td valign="top" width="319">Stock Plant</td>
<td valign="top" width="319">Distribution</td>
</tr>
<tr>
<td valign="top" width="319">Alstonia spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Alstonia angustifolia</td>
<td valign="top" width="319">Old World</td>
</tr>
<tr>
<td valign="top" width="319">Alstonia scholaris</td>
<td valign="top" width="319">Southeast Asia</td>
</tr>
<tr>
<td valign="top" width="319">Aspidosperma</td>
<td valign="top" width="319">South America</td>
</tr>
<tr>
<td valign="top" width="319">quebracho-blanco</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Catharanthus lanceus</td>
<td valign="top" width="319">North America</td>
</tr>
<tr>
<td valign="top" width="319">Corynanthe spp.</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">Mitragyna stipulosa</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">(cf.palm wine)</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Pausinystalia yohimba</td>
<td valign="top" width="319">West Africa</td>
</tr>
<tr>
<td valign="top" width="319">Pausirtystalia· macroceras</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Pausinystaliatrillesii</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia spp.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia macrophylla</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">Stapf</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia serpentina</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Benth.</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Rauvolfia volkensii</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">Vincaspp.</td>
<td valign="top" width="319">Africa</td>
</tr>
<tr>
<td valign="top" width="319">(cf. Catharanthus roseus)</td>
<td valign="top" width="319"> </td>
</tr>
</tbody>
</table>
Literature

See also the entries for Alstonia scholaris, Corynanthe

spp., and Pausinystalia yohimba.

Buffum, John. 1982. Pharmacosexology: The effects

of drugs on sexual function-a review. Journal of

Psychoactive Drugs 14 (1-2): 5-44.

Finch, N., and W. I. Taylor. 1962. Oxidative

transformation of indole alkaloids. 1:

Preparation of oxindoles from yohimbine.

Journal of the American Chemical Society

84:3871-77.

Hofmann, Albert. 1954. Die Isolierung weiterer

Alkaloide aus Rauwolfia serpentina Benth.

Helvetica Chimica Acta 37:849-65.

Lambert, G. A., W. J. Lang, E. Friedman, E. Meller,

and S. Gershon. 1978. Pharmacological and

biological properties of isomeric yohimbine

alkaloids. European Journal ofPharmacology

49:39-48.

Leary, Timothy. 1985. Auf der Suche nach dem

wahren Aphrodisiakum und e1ektronischer Sex.

Sphinx Magazin 35.

Miller, W. W. 1968. Afrodex in the treatment of male

impotence: A double-blind cross-over study.

Current Therapeutic Research 10:354-59.

Poisson, J. 1964. Recherches recentes sur les

alcaloYdes du pseudocinchona et du yohimbine.

Ann. Chim. 9:99-121.

Porst, H. 1996. Orale und intracavernose

Pharmakotherapie. TW Urologie Nephrologie 8

(2): 88-94.

Sobotka, J. J. 1969. An evaluation of Afrodex in the

management of male impotency: A double-blind

cross-over study. Current Therapeutic Research

11:87-94.

Timmins, Peter, and William E. Court. 1974.

Alkaloids of Rauwolfia macrophylla.

Phytochemistry 13:281-82.

Weyers, Wolfgang. 1982. Die Empfehlung in der

Selbstmedikation. Heusenstamm: Keppler Verlag.</td>
</tr>

</table>

Ephedrine

2013-01-13T18:19:57Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Aphetonin, efedrina, ephedrin, ephedrine,

ephedrinum, ephetonin, erythro-2-methylaminoI-

hydroxyl-l-phenylpropane, (IR,2S)-2-methylamino-

l-phenyl-l-propanol

Empirical formula: ClQH1SNO

Substance type: ephedra alkaloid

Ephedrine was first isolated in 1887 by Nagai from

Ephedra distachya (cf. Ephedra spp.) and was first

introduced into ophthalmology as Mydriaticum

(cf. atropine). Since around 1925, the alkaloid also

been an important asthma medication (Schneider

1974,2:54*).

Ephedrine occurs in almost all species of

ephedra (cf. Ephedra gerardiana, Ephedra sinensis,

Ephedra spp.). Two Malvaceae, Sida acuta Burm.

and Sida rhombifolia 1. (Sida spp.), which are

smoked along the Mexican Gulf Coast as a lTlarijuana

substitute (cf. Cannabis indica), also

contain ephedrine (Schultes and Hoffmann 1992,

56*). Ephedrine is probably present in other

species of Sida as well. Ephedrine has also been

found in Aconitum spp., yew (Taxus bacata L.; cf.

witches' ointments), and khat (Catha edulis)

(Rompp 1995, 1191*; Roth et al. 1994,695*).

Ephedrine has sympathomimetic effects and

causes an increased excretion of the endogenous

neurotransmitter noradrenaline, which is responsible

for the stimulant effects (Kalix 1991). Ephedrine

hydrochloride has potent stimulant effects;

it improves the general mood and may even

induce euphoria. These effects can last up to eight

hours. It is known that "therapeutic overdoses of

ephedrine (Aphetonin) can also cause pronounced

states of excitation combined with sexual arousal"

(Fiihner 1943, 199*). In men, however, ephedrine

induces a temporary state of impotence. Ephedrine

is a popular doping agent for athletes but is

prohibited for this purpose (Korner 1994, 1483*).

There have been reports of "ephedrine addiction"

(Prokop 1968).

Because ephedrine helps reduce swelling of the

mucous membranes, it is a component of rnany

cough syrups (see codeine). Ephedrine suppresses

the effects of alcohol and is administered subcutaneously

to prevent hypotension during anesthesia

(Morton 1977,35*). Between 55 and 75% of ephedrine

is excreted in the urine unchanged (Roth et

al. 1994, 812*). The effective oral dosage is 5 to

10 mg.

The closely related ephedra alkaloids have

similar effects but vary in their potency (Reti 1953). Pseudoephedrine is significantly weaker,

while the related ephedroxanes tend to have

depressant effects (Hikino et al. 1985). Pseudoephedrine

can be used to produce methcathinone,

which in the United States is smoked as "speed" or

snuffed like cocaine (it is also used as a substitute

for cocaine) (Glennon et al. 1987).

Although Catha edulis does contain d- norisoephedrine,

it is not the plant's primary active constituent,

as was previously assumed (Wolfes 1930).

However, cathinone, the psychoactive constituent

in khat leaves, is metabolized into ephedrinene

(Brenneisen et al. 1986; Kalix 1991). Norephedrine,

the nor-form (a threo-isomer) of ephedrine, lacks

a methyl group on the side chain. Up to 90% of

norephedrine is excreted unchanged (Cho and

Segal 1994, 58).

Removing the hydroxyl group from the

ephedrine molecule by either reduction or ~hydroxylation

yields amphetamine (Cho and Segal

1994,57). Amphetamine is one of the most highly

effective stimulants known. Numerous derivatives

have been developed from amphetamine (e.g.,

Ritalin, methamphetamine, MDMA; cf. herbal

ecstasy). In addition to their stimulating effects,

several of these substances also induce

empathogenic and even hallucinogenic effects

(Cho and Segal 1994). Amphetamine has not yet

been found to occur in nature.</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Ephedrine is available as anhydrous ephedrine

(ephedrinum anhydricum), ephedrine hemihydrate,

or (most often) ephedrine hydrochloride

([ +] -ephedrine-HCL). Ephedrine and ephedrine

preparations (medicinal drugs) require a prescription.

Because ephedrine is now regarded as a

precursor substance for the illegal synthesis of

MDMA, it is only rarely prescribed and is strictly

controlled. In Germany, only combination preparations

(cough medicines) in which a single

dosage may not exceed 10 mg of ephedrine can be

purchased in a pharmacy without prescription

(Roth et al. 1994, 812*). A number of high-profile

cases, including one in which a young professional

athlete died after ingesting ephedrine before training,

resulted in the banning of most ephedrine

preparations in the United States in 2004.

Literature

See also the entries for Catha edulis, Ephedra

gerardiana, Ephedra sinica, and Ephedra spp.

Brenneisen, R., S. Geisshusler, and X. Schorno. 1986.

Metabolism of cathinone to (-)-norephedrine

and (-)-norpseudoephedrine. Journal of

Pharmacy and Pharmacology 38:298-300.

Cho, Arthur K., and David S. Segal, eds. 1994.

Amphetamine and its analogs:

Psychopharmacology, toxicology and abuse. San

Diego: Academic Press.

Costa, E., and S. Garattini, eds. 1970. Amphetamine

and related compounds. New York: Raven Press.

Glennon, R., M. Yousif, N. Naiman, and P. Kalix.

1987. Methcathinone, a new and potent

amphetamine-like agent. Pharmacol. Biochem.

Behav.26:547-51.

Hikino, Hiroshi, Kuniaki Ogata, Yoshimasa

Kasahara, and Chohachi Konno. 1984.

Pharmacology of ephedroxanes. Journal of

Ethnopharmacology 13:175-9l.

Hofmann, H., K. Opitz, and H. J. Schnelle. 1955. Die

Wirkung des nor-c-Ephedrins. ArzneimittelForshung

5:367-70.

Kalix, P. 1991. The pharmacology of psychoactive

alkaloids from Ephedra and Catha. Journal of

Ethnopharmacology 32:201-8.

Panse, E, and W. Klages. 1964. Klinischpathologische

Beobachtungen bei chronischem

MiBbrauch von Ephedrin. Archiv fur Psychiatrie

und Neurologie 206:69 ff.

Prokop, H. 1968. Halluzinose bei Ephedrinsucht. Der

Nervenarzt 1968:71 ff.

Reti, L. 1953. Ephedra bases. In The alkaloids:

Chemistry and physiology, ed. R. H. E Manske

and H. L. Holmes, 339-62. New York: Academic

Press.

Wolfes, 0.1930. Uber das Vorkommen von dNorisoephedrin

in Catha edulis. Archiv der

Pharmazie 268:81-83.</td>
</tr>

</table>

Withanolides

2013-01-13T18:18:48Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

DivinorinA

Substance type: diterpene (derodane)

Salvinorin A is the active constituent in Salvia

divinorum. Apart from THe and the constituents

in essential oils, it is the only known nonnitrogenous

psychoactive plant constituent.

Salvinorin is not an alkaloid.

The substance was first described by Ortega et

al., who named it salvinorin (1982). The same

substance was subsequently described under the

name divinorin A (Valdes et al. 1984). Salvinorin

A is extracted from fresh plant material. The

effective dosage is between 200 and 500 /-Lg.

Salvinorin A can be smoked in a glass pipe; a

better technique involves vaporizing the plant and

then inhaling the fumes. It can also be taken in

solution under the tongue. When the substance is

smoked or inhaled, the effects are immediately

apparent, and the primary effects last from five to

ten minutes. When it is administered sublingually,

the effects become manifest after about ninety

seconds and reach their peak some ten to fifteen

minutes later, after which they gradually diminish

(Turner 1996).

The potent and strange psychoactive effects of

salvinorin A were probably discovered by Daniel

Siebert:

Salvinorin A is an extremely powerful compound

for altering consciousness. In fact, it is

the most potent naturally occurring hallucinogen

that has been isolated to date. But

before potential experimenters become too

interested, it must be clearly stated that the

effects are often extremely unnerving and that

there is a very real risk that persons may

physically harm themselves when using it....

I have seen people get up and jump across

the room, thereby falling over the furniture,

babbling incomprehensible nonsense, and

hitting their heads against the wall. Several

people tried to leave the house. When the

experience was over, they did not remember what had happened. In fact, they actually

believed that they remembered entirely different

events. To an outside observer, it appears

as though these people have an emptyexpression

in their eyes, as though they are not

present (and perhaps they really are not).

(Siebert 1995,4)

This description is strongly remInIscent of

phenomena that occur with high dosages (overdoses)

of nightshades (Atropa belladonna, Brugmansia

spp., Hyoscyamus niger, Datura spp.) and

the tropane alkaloids atropine and scopolamine.

Most subjects have no desire at all to repeat an

experiment with salvinorin.

The neurochemistry of salvinorin A is still

unresolved. In spite of extensive receptor testing

(NovaScreen method), salvinorin A has not been

found to bind to any known neurotransmitter

receptors, including the receptor that ketamine

occupies (David Nichols, pers. comm.). The daring

and extreme experiments of D. M. Turner suggest

that salvinorin A does not have any negative crosstolerance

with other psychoactive substances (such

as LSD, N,N-DMT, ketamine) (Turner 1996).</td>
<td valign="top" width="53%">Commercial Forms and Regulations

None

Literature

See also the entries for Coleus blumei, Salvia divinorum,

and diterpenes.

Ortega, A., J. F. Blount, and P. S. Marchand. 1982.

Salvinorin, a new trans-neoclerodane diterpene

from Salvia divinorum (Labiatae). Journal ofthe

Chemical Society, Perkin Transactions 1:2505-8.

Siebert, Daniel J. 1995. Salvinorin A: Vorsicht

geboten. Entheogene 3:4-5.

Turner, D. M. 1996. Salvinorin: The psychedelic

essence ofSalvia divinorum. San Francisco:

Panther Press.

Valdes, Leander, William M. Butler, George M.

Hatfield, Ara G. Paul, and Masato Koreeda. 1984.

Divinorin A, a psychotropic terpenoid, and

divinorin Bfrom the hallucinogenic Mexican

mint Salvia divinorum. Journal ofOrganic

Chemistry 49 (24): 4716-20.</td>
</tr>

</table>

Scopoletin

2013-01-13T18:17:31Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Hyoscin, (-)-hyoscin, hyoscine, hyoszin, L6(-),7epoxytropin-

tropate, I-hyoscine, scopolamin, [7(S)(

la,213,413,5a,713)] -a-(hydroxymethyl)benzeneacetic

acid 9-methyl-3-oxa-9-azatricyclo- [3.3.1.02,4]

non-7-ylester, skopolamin, tropane acid ester of

skopolin

Substance type: tropane alkaloid

Scopolamine was first isolated in 1888 by E. Schmidt

from the roots of (( Scopolia atropoides" (= Scopolia

carniolica). It is very closely related to atropine

and is a characteristic component of plants from

the Nightshade Family (Solanaceae), especially the

psychoactive species. For the pharmaceutical

industry, the most important sources of scopolamine

are the Australian duboisias (Duboisia spp.),

the dried leaves of which can contain up to 70/0

alkaloids. Scopolamine is also produced by the

recrystallization of hyoscyamine.

For medicinal purposes, scopolamine is

administered at dosages of 0.5 to 1 mg, with a total

daily maximum dosage of 3 mg. The lowest lethal

dosage for humans is about 14 mg (Roth et a1.

1994:921*).

Scopolamine is a very potent hallucinogen that Leuner (1981 *) classified as a "Class II" hallucinogen

because of its simultaneously hallucinogenic

and narcotic/consciousness-clouding effects (cf.

also Dittrich 1996*).

According to Hunnius, scopolamine is utilized

in medicine as a hypnotic agent, especially for

cases of "agitated states in the mentally ill, for

Parkinson's and paralysis agitans, and for treating

withdrawal of morphine users" (Hunnius 1975,

609*).

In contrast to atropine, which initially stimu1ates

the central nervous system, scopolamine

induces predominantly a narcotic paralysis

from the beginning, which is why it serves as a

"chemical straitjacket" for agitated mental

patients. Delirium and hallucinations are not

infrequently seen ... with therapeutic application.

. . . Chronic scopolamine poisoning

with gradually increasing dosages leads to

psychoses with hallucinations. (Fiihner 1943,

202 f.*)

In the former East Germany, scopolamine was

still being used as a "chemical straightjacket" in the

1980s (Ludwig 1982, 148*; Schwarz 1984). Scopolamine

may be combined with morphine for

the same purpose (Rompp 1950, 264*). A combination

of scopolamine hydrobromide and morphine

hydrochloride is used as a preoperative

anesthesia (cf. soporific sponge). Recent tests with

mice found that scopolamine hydrobromide causes

a marked increase in anxiety as compared to

scopolamine methylbromide (Rodgers and Cole

1995).

To treat motion sickness-a use to which

scopolamine has long been put (Rompp 1950,

265*)-an adhesive patch was developed that

contains 1.5 mg scopolamine and can be adhered

behind the ear as needed. The active component is

absorbed through the skin into the blood vessels

of the ear region and affects the organs of balance

in the ear. This property of scopolamine supports

the idea that the constituents found in witches'

ointments could be absorbed when the mixtures

were rubbed onto the skin.

Scopolamine was a popular inebriant in the

Munich jazz scene of the 1950s. Because the

dosages used were often so high, many of the concerts

had to end early.</td>
<td valign="top" width="53%">Plants CQl1tail1ing. Scop.olall1ine

(from Festi1995*;Hagemann et a1. 1992; Ripperger 1995; supplemented)
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0">
<tbody>
<tr>
<td valign="top" width="319">LORANTHACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Benthamia alyxifolia</td>
<td valign="top" width="319">leaves</td>
</tr>
<tr>
<td valign="top" width="319">SOLANACEAE</td>
<td valign="top" width="319"> </td>
</tr>
<tr>
<td valign="top" width="319">Anthoceris ilicifolia Hook.</td>
<td valign="top" width="319">root</td>
</tr>
<tr>
<td valign="top" width="319">Atropa belladonna (L-scopolamine)</td>
<td valign="top" width="319">root</td>
</tr>
<tr>
<td valign="top" width="319">Atropanthe sinensis (Hems1.) Pascher</td>
<td valign="top" width="319">fruits, root</td>
</tr>
<tr>
<td valign="top" width="319">Brugmansia (all species)</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Datura stramonium</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Daturaspp.</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Duboisia hopwoodii</td>
<td valign="top" width="319">leaves</td>
</tr>
<tr>
<td valign="top" width="319">Duboisia spp.</td>
<td valign="top" width="319">leaves, bark</td>
</tr>
<tr>
<td valign="top" width="319">Hyoscyamus niger</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Hyoscyamus spp.</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Iochroma fuchsioides</td>
<td valign="top" width="319">leaves</td>
</tr>
<tr>
<td valign="top" width="319">Iochroma spp.</td>
<td valign="top" width="319">?</td>
</tr>
<tr>
<td valign="top" width="319">Latua pubiflora</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Lycium barbarum 1. [syn. Lycium halimifolium Mil1.]</td>
<td valign="top" width="319">entire plant</td>
</tr>
<tr>
<td valign="top" width="319">Mandragora officinarum</td>
<td valign="top" width="319">root</td>
</tr>
<tr>
<td valign="top" width="319">Mandragora chinghaiensis Kuang et Lu (cf. Mandragora spp.)</td>
<td valign="top" width="319">root</td>
</tr>
<tr>
<td valign="top" width="319">Scopolia carniolica (= Scopolia atropoides)</td>
<td valign="top" width="319">root</td>
</tr>
<tr>
<td valign="top" width="319">Solandra spp.</td>
<td valign="top" width="319">entire plant</td>
</tr>
</tbody>
</table>
Commercial Forms and Regulations

The alkaloid is available as scopolamine hydrobromide

and scopolamine hydrochloride. Pharmacies

usually carry these substances in the form of small flasks for use in injections. Scopolamine

requires a prescription.

Literature

See also the entries for Atropa belladonna, cocaine,

and tropane alkaloids.

Flicker, C., M. Serby, and S. H. Ferris. 1990.

Scopolamine effects on memory, language,

visuospatial praxis and psychomotor speed"

Psychopharmacology 100:243-50.

Hagemann, K., K. Piek, J. StOckigt, and E. W. Weiler.

1992. Monoclonal antibody-based enzyme

immunoessay for the quantitative determination

of the tropane alkaloid, scopolamine. Planta

Medica 58:68-72.

Heimann, Hans. 1952. Die Skopolaminwirkung. Basel

and New York: S. Karger.

Keeler, M. H., and F. J. Kane. 1968. The use of

hyoscyamine as a hallucinogen and intoxicant.

American Journal ofPsychiatry 124:852-54.

Ripperger, Helmut. 1995. (5)-scopolamine and (5)norscopolamine

from Atropanthe sinensis. Planta

Medica 61:292-93.

Rodgers, R. J., and J. C. Cole. 1995. Effects of

scopolamine and its quaternary analogue in the

murine elevated plus-maze test of anxiety.

Behavioral Pharmacology 6:283-89.

Schwarz, H.-D. 1984. Hyoscin (= Scolpolamin) statt

Zwangsjacke. Zeitschrift fur Phytotherapie 5 (3):

840-41.</td>
</tr>

</table>

Indole Alkaloids

2013-01-13T18:16:07Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Indolalkaloide, indolamine alkaloids, indole,

indoles

Indole alkaloids are derived from the indole ring

system and appear almost exclusively in the

families Apocynaceae501 (Alchornea spp., Alstonia

scholaris, Aspidosperma quebracho-blanco, Catharanthus

roseus, Rauvolfia spp., Tabernaemontana

spp., Tabernanthe iboga, Vinca spp., Voacanga spp.),

Loganiaceae (Gelsemium sempervirens, Strychnos

nux-vomica, Strychnos spp.), and Rubiaceae (Corynanthe

spp., Mitragyna speciosa, Pausinystalia

yohimba). Indole alkaloids also occur in certain

ascomycetes (Balansia cyperii, Claviceps paspali,

Claviceps purpurea, Claviceps spp.), other fungi

(Tyler 1961), and several climbing vines (Ipomoea

violacea, Turbina corymbosa) (Hofmann 1966; cf.

ergot alkaloids).

Included among the large group of indole alkaloids

(Trojanek and Blaha 1966) are the ~-carbolines

with harmaline and harmine; the tryptamine

derivates bufotenine, N,N-DMT, 5-MeO-DMT,

psilocybin, and psilocin; the ergot alkaloids; and

the alkaloids of the ibogane type (ibogaine, voacangine),

yohimbane type (yohimbine), and

strychnane type (strychnine). Indoles are also found

in the genus Uncaria, several species of which are

used as ayahuasca additives (Phillipson and

Hemingway 1973).

Many indole alkaloids are psychoactive or

occur in plants that are utilized for traditional

psychoactive purposes (Lindgren 1995; Rivier and

Pilet 1971; Schultes 1976).</td>
<td valign="top" width="53%">Literature

See also the entries for ~-carbolines, ergot

alkaloids, and yohimbine.

Gershon, S., and W. J. Lang. 1962. A

psychopharmacological study of some indole

alkaloids. Archives Internationales de Pharmacodynamie

et de Therapie 135 (1-2): 31-56.

Hesse, M. 1968. Indolalkaloide in Tabellen. Berlin:

Springer.

Hofmann, Albert. 1966. AlcaloYdes indoliques isoles de

plantes hallucinogenes et narcotiques du Mexique.

In Colloques internationaux du Centre National de

la Recherche Scientifique: Phytochimie et plantes

medicinales des terres du Pacifique, Nomea

(Nouvelle Caledonie) 28.4-5.5.1964, 223-41. Paris:

Centre National de la Recherche Scientifique.

Lindgren, Jan-Erik. 1995. Amazonian psychoactive

indols: A review. In Ethnobothany: Evolution ofa

discipline, ed. Richard Evans Schultes and Siri von

Reis, 343-48. Portland, Ore.: Dioscorides Press.

Phillipson, John David, and Sarah Rose Hemingway.

1973. Indole and oxindol alkaloids from Uncaria

bernaysia. Phytochemistry 12:1481-87.

Rivier, Laurent, and Paul-Emile Pilet. 1971.

Composes hallucinogenes indoliques naturels.

Annee BioI. 3:129-49.

Schultes, Richard Evans. 1976. Indole alkaloids in

plant hallucinogens. Journal ofPsychedelic Drugs

80 (1): 7-25.

Trojanek, J., and K. Blaha. 1966. A proposal for the

nomenclature of indole alkaloids. Lloydia 29 (3):

149-55.

Tyler, Varro E. 1961. Indole derivatives in certain

North American mushrooms. Lloydia 24:71-74.</td>
</tr>

</table>

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== Entheogens ==
* [[Gold Pepper]]
* [[Kougoed]]
* [[Scopolia]]
* [[Cup of Gold]]
* [[Ska Maria Pastora]]
* [[Sassafras Tree]]

==[[Compounds]]==
* [[B-Carbolines]]
* [[THC]]
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* [[Indole Alkaloids]]
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__NOTOC__
__NOEDITSECTION__

Ergot Alkaloids

2013-01-13T18:02:36Z

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Ergoline, ergoline alkaloids, ergot alkaloids,

ergotalkaloide, mutterkornalkaloide

Ergot alkaloids are derivatives of lysergic acid or

clavine derivatives and belong to the group of

indole alkaloids. They are found in many climbing

plants (Convolvulaceae) and fungi (Claviceps purpurea,

Claviceps paspali, Claviceps spp.). The ergot

alkaloids can be divided into two groups that

exhibit stark pharmacological differences. One

group is composed of alkaloids that are highly

toxic and cause gangrenous ergotism, while the

other group consists of psychoactive alkaloids with

hallucinogenic effects. Both types may be present

in the same plant (Hofmann 1964).

The following ergot alkaloids have been found

in the Convolvulaceae: agroclavine, ergine, ergonovine,

isoergine (= isolysergic acid amide),

chanoclavine I and II, racemic chanoclavine II,

elymoclavine, festuclavine, lysergene, lysergol, isolysergol,

molliclavine, penniclavine, cycloclavine,

stetoclavine, isostetoclavine, ergometrinine, lysergic

acid-a-hydroxyethylamide (= lysergic acid methylcarbinolamide),

isolysergic acid-a-hydroxyethylamide

(= isolysergic acid methylcarbinolamide),

ergosine, and ergosinine (cf. Argyreia nervosa,

Convolvulus tricolor, Ipomoea violacea, Ipomoea

spp., Turbina corymbosa).

One hallucinogenic ergot alkaloid is ergonovine

(ergometrine, D-Iysergic acid-L-2-propanolamide,

ergobasin, ergotocine, ergostetrine, ergotrate, syntometrine,

N- [a -(hydroxymethyl)ethyl] -D-Iysergic

amide). Ergonovine maleate is psychoactive at

dosages between 3 and 10 mg (Bigwood et al.

1979). The semi-synthetic methylergonovine has

also been reported to induce psychoactive effects

(Ott and Neely 1980).

Ergine (= lysergic acid amide, LSA, lysergic

amide, 9,10-didehydro-6-methylergoline-8~-carboxamide)

induces psychoactive effects reminiscent

of those produced by LSD (lysergic acid

diethylamide). LSD is a slight chemical variant of

lysergic acid amide that can be produced from

ergot (Claviceps purpurea). LSD is a psychopharmaca,

a "remedy for the soul" (Albert Hofmann)

whose entheogenic effects are very well known

(Hofmann 1979*).

The ergot alkaloids dihydroergotaminemesilate,

dihydroergotamintartrate, ergometrine hydrogenmaleate,

and ergotamine tartrate have a variety of

uses in medicine, including as treatments for labor

contractions and migraines.</td>
<td valign="top" width="53%">Commercial Forms and Regulations

Ergonovine requires a prescription. In the United

States, ergine is a controlled substance (Ott 1993,

437*). LSD is illegal throughout the world.

Literature

See also the entries for Claviceps paspali, Claviceps

purpurea, and indole alkaloids.

Bigwood, Jeremy, Jonathan Ott, Catherine

Thompson, and Patricia Neely. 1979.

Entheogenic effects of ergonovine. Journal of

Psychedelic Drugs 11 (1-2): 147-49.

Hofmann, Albert. 1964. Die Mutterkorn-Alkaloide.

Stuttgart: Enke.

Ott, Jonathan, and Patricia Neely. 1980. Entheogenic

(hallucinogenic) effects of methylergonovine.

Journal ofPsychedelic Drugs 12 (2): 165-66.

Rivier, 1. 1984. Ethnopharmacology of LSD and

related compounds. In 50 years ofLSD: Current

status and perspectives ofhallucinogens, ed. A.

Pletscher and D. Ladewig, 43-55. NewYork and

London: Parthenon Publishing.

Yui, T., and Y. Takeo. 1958. Neuropharmacological

studies on a new series of ergot alkaloids.

Japanese Journal ofPharmacology 7: 157.</td>
</tr>

</table>

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** [[Cannabis]]
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** [[GHB]]

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** [[Oxycodone]]
** [[Fentanyl]]

* [[Psychedelics]]
** [[LSD]]
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** [[Salvia]]
** [[2C-X|2C-X series]]
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* [[Deliriants]]
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** [[Diphenhydramine]]

</td>

<td valign=top width=15%>
== Entheogens ==
* [[Gold Pepper]]
* [[Kougoed]]
* [[Scopolia]]
* [[Cup of Gold]]
* [[Ska Maria Pastora]]
* [[Sassafras Tree]]

==[[Compounds]]==
* [[B-Carbolines]]
* [[THC]]
* [[Tropane Alkaloids]]
* [[Psilocybin/Psilocin]]
* [[Ergot Alkaloids]]
</td>

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</table>

__NOTOC__
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Psilocybin/Psilocin

2013-01-13T17:43:59Z

205.56.181.196: Created page with "<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0"> <tr> <td valign="top" width="50%">O..."

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Psilocybin: CY-39, indocybin, 0-phosphoryl-4hydroxy-

N,N-dimethyltryptamine, 3(2-dimethylamino)

ethylindol-4-01 dihydrogenphosphatester

Psilocin: 4-hydroxy-N,N-dimethyltryptamine,

psilocine, psilocyn (misspelling in the legal literature),

3- [2-(dimethylamino)ethyl]-1H-indole-4-01

Empirical formula: C12H17N204P (psilocybin),

C12H16N20 (psilocin)

Substance type: tryptamines, indole amines (indole

alkaloids)

Psilocybin was first isolated from Psilocybe mexicana

and identified by Albert Hofmann in 1955

(Hofmann et al. 1958, 1959). The phosphorylated

indole amine psilocybin is transformed into

psilocin by splitting off the phosphoric acid group

(Hofmann and Troxler 1959). Because the

protection the phosphoric acid would provide is

lacking, psilocin easily oxidizes with the phenolic hydroxyl group, resulting in blue quinonoid products.

This explains why psilocybin mushrooms

turn blue after they have been squeezed and

harvested (cf. Panaeolus cyanescens, Psilocybe cyanescens).

In the body, psilocybin is immediately

metabolized into psilocin, which is the actual

psychoactive constituent.

Psilocybin and psilocin are closely related to

baeocystin (= 0-phosphoryl-4-hydroxy-N-methyltryptamine,

norpsilocybin), which probably represents

the biogenic precursor of psilocybin (Repke

et al. 1977; cf. also Brack et al. 1961 and Chilton et

al. 1979). Baeocystin may be a derivative of tryptophan

(Brack et al. 1961).

The usual psychedelic dosage of psilocybin is

10 mg. When psilocybin is taken orally, the effects

typically become apparent in about twenty

minutes504 (Shulgin 1980). Rudolf Gelpke (19281972)

took between 6 and 20 mg during his selfexperiments;

with 10 mg, he made his historic

"journey to the outer space of the soul": This inebriation was a space flight not into the

outer realm, but into the inner person, and for

a moment I experienced reality from a

position located somewhere beyond the

gravity of time. (Gelpke 1962,395)

With very high dosages, it is common to perceive

voices (Beach 1997). This could explain why

Indians say that the mushroom talks to them.

Toxic dosages are unknown!

Walter Pahnke's "Good Friday experiment," in

which theology students were administered psilocybin

in a church on Good Friday, has become

renowned. Pahnke applied the theory of dosage,

set, and setting as part of the test to see whether

mystical revelations would occur, which was

indeed the case (Pahnke 1972; Pahnke and

Richards 1970; cf. Doblin 1991).

Timothy Leary and his colleagues at Harvard

experimented with psilocybin on prisoners. Their

experiments were aimed at determining whether

the psychedelic constituent was suitable for use in

therapy with inmates. It was hoped that the drug

experience would enable the prisoners to attain

insights into their behavior that would then enable

them to change themselves on their own. Although

these experiments showed great promise, they had

to be terminated (Clark 1970; Forcier and Doblin

1994; Riedlinger and Leary 1994).

Both psilocybin and two synthetic derivatives

(CZ-74, CY-19) have been used with success in

psychedelic and psycholytic therapy (Leuner 1963;

Leuner and Baer 1965; Passie 1995, 1996). Psilocybin

can release, stimulate, and inspire creativity

(Fischer et al. 1972), as an increasing number of

studies have shown (Baggott 1997; Spitzer et al.

1996), and "archetypal art therapy" is making use

of this effect (Allen 1995).

Today, psilocybin is playing a central role in

neurochemical research into brain activity, in

which it is being studied with the very elaborate

and costly positron-emission tomography (PET)

method (Vollenweider 1996).

Jochen Gartz has discovered that fungal

enzymes synthesize the "synthetic" psilocin analog

CZ-74 (diethyl-4-hydroxytryptamine, 4-0H-DET)

from diethyltryptamine when it is added to a

Psilocybe spp. substrate 0. Gartz, pers. comm.). It

is possible that the "synthetic" CY-19 (= diethyl-4phosphoryloxytryptramine)

can be produced in

the same fashion.

Commercial Forms and Regulations

Both psilocybin and psilocin are classified as

Schedule I drugs in the United States (Shulgin

1980). They are internationally regarded as illegal

"narcotics." The analog substances psilocin-(eth)

and psilocybin-(eth) are also illegal (Korner 1994,

40*).</td>
<td valign="top" width="53%">Literature

See also the entries for Psilocybe mexicana and

Psilocybe spp.

Allen, Tamara D. 1994. Research in archetypal art

therapy with psilocybin. Maps 5 (1): 39-40.

---.1995. Archetypal art therapy: Hearing

psilocybin in the art & metaphor work of

volunteer no. 31. Maps 6 (1): 23-26.

Baggot, Matthew. 1997. Psilocybin's effects on

cognition: Recent research and its implications

for enhancing creativity. Maps 7 (1): 10-11.

Beach, Horace. 1997. Listening for the logos: Study

of reports of audible voices at high doses of

psilocybin. Maps 7 (1): 12-17.

Bocks, S. M. 1968. The metabolism of psilocin and

psilocybin by fungal enzymes. Biochemical

Journal 106:12-13.

Borner, Stefan, and Rudolf Brenneisen. 1987.

Determination of tryptamines in hallucinogenic

mushrooms using high-performance liquid

chromatography with photodiode array

detection. Journal ofChromatography 408:402-8.

Brack, A., Albert Hofmann. F. Kalberer, H. Kobel,

and J. Rutschmann. 1961. Tryptophan als

biogenetische Vorstufe des Psilocybins. Archiv der

Pharmazie 294/66 (4): 230-34.

Chilton, W. Scott, Jeremy Bigwood, and Robert E.

Jensen. 1979. Psilocin, bufotenine, and serotonin:

Historical and biosynthetic observations. Journal

ofPsychedelic Drugs 11 (1-2): 61-69.

Clark, Jonathan. 1970. Psilocybin: The use of

psilocybin in a prison. In Psychedelics, ed.

Bernard Aaronson and Humphry Osmond,

40-44. Garden City, N.Y.: Anchor Books.

Doblin, Rick. 1991. Pahnke's (Good Friday

experiment': Along-term follow-up and

methodological critique. The Journal of

Transpersonal Psychology 23 (1): 1-28.

Fischer, Roland, Ronald Fox, and Mary Ralstin. 1972.

Creative performance and the hallucinogenic

drug-induced creative experience. Journal of

Psychedelic Drugs 5 (1): 29-36. (On psilocybin

and creativity research.)

Forcier, Michael W., and Rick Doblin. 1994. Longterm

follow-up to Leary's Concord Prison

psilocybin study. Maps 4 (4): 20-21.

Gelpke, Rudolf. 1962. Von Fahrten in den Weltraum

der Seele: Berichte tiber Selbstversuche mit

Delysid (LSD) und Psilocybin (CY). Antaios

3:393-411.

---. [1997]. Von Fahrten in den Weltraum der

Seele: Berichte uber Selbstversuche mit LSD und

Psilocybin. Lohrbach: Werner Pieper's

MedienXperimente and Edition Rauschkunde.

Gnirss, Fritz. 1959. Untersuchung mit Psilocybin,

einem Phantastikum aus dem mexikanischen

Rauschpilz Psilocybe mexicana. Schweizer Archiv

fur Neurologie, Neurochirurgie und Psychiatrie

84:346-48.

Hofmann, Albert, A. Frey, H. Ott, Th. Petrzilka, and

F. Troxler. 1958. Konstitutionsautklarung und

Synthese von Psilocybin. Experientia 14 (11):

397-401.

Hofmann, Albert, Roger Heim, A. Brack, and H.

Kobel. 1958. Psilocybin, ein psychotroper

Wirkstoff aus dem mexikanischen Rauschpilz

Psilocybe mexicana Heim. Experientia 14 (3):

107-12.

Hofmann, Albert, Roger Heim, A. Brack, H. Kobel,

A. Frey, H. Ott, T. Petrzilka, and F. Troxler. 1959.

Psilocybin und Psilocin, zwei psychotrope

Wirkstoffe aus mexikanischen Rauschpilzen.

Helvetica Chimica Acta 42 (162): 1557-72.

Hofmann, Albert, and F. Troxler. 1959.

Identifizierung von Psilocin. Experientia 15 (3):

101-4.

Jones, Richard. 1963. "Up" on Psilocybin. The

Harvard Review 1 (4): 38-43.

Krippner, Stanley. 1970. Psilocybin: An adventure in

psilocybin. In Psychedelics, ed. Bernard Aaronson

and Humphry Osmond, 35-39, Garden City,

N.Y.: Anchor Books.

Laatsch, Hartmut. 1994. Das Fleisch der GotterVon

den Rauschpilzen zur Neurotransmission. In

Welten des Bewufitseins, ed. A. Dittrich et aI.,

3:181-95. Berlin: VWB.

---. 1996. Zur Pharmakologie von Psilocybin

und Psilocin. In Maria Sabina-Botin der heiligen

Pilze, ed. Roger Liggenstorfer and Christian

R~itsch, 193-202. Solothurn: Nachtschatten

Verlag.

Leuner, Hanscarl. 1963. Die Psycholytische Therapie:

Klinische Psychotherapie mit Hilfe von LSD-25

und verwandten Substanzen. Zeitschrijt fur

Psychotherapie und medizinische Psychologie

13:57 ff.

Leuner, Hanscarl, and G. Baer. 1965. Two shortacting

hallucinogens of the psilocybin-group. In

Neuro-pharmacology, ed. D. Bente and P. B.

Bradley. Amsterdam: Elsevier.

Ott, Jonathan, and Gaston Guzman. 1976. Detection

of psilocybin in species of Psilocybe, Panaeolus

and Psathyrella. Lloydia 39:258-60.

Pahnke, Walter N. 1972. Drogen und Mystik. In

Josuttis and Leuner, 54-76*.

Pahnke, Walter N., and William A. Richards. 1970.

Implications of LSD and experimental

mysticism. Journal ofPsychedelic Drugs 3 (1):

92-108.

Passie, Torsten. 1995. Psilocybin in der westlichen

Psychotherapie. Curare 18 (1): 131-52.

---. 1996. Psilocybin in der westlichen

Psychotherapie. In Maria Sabina-Botin der

heiligen Pilze, ed. Roger Liggenstorfer and

Christian R~itsch, 211-25. Solothurn:

Nachtschatten Verlag.

Repke, David B., Dale Thomas Leslie, and Gaston

Guzman. 1977. Baeocystin in Psilocybe, Conocybe

and Panaeolus. Lloydia 40 (6): 566-78.

Riedlinger, Thomas, and Timothy Leary. 1994.

Strong medicine for prisoner reform: The

Concord Prison experiments. Maps 4 (4): 22-25.

Shulgin, Alexander T. 1980. Psilocybin. Journal of

Psychedelic Drugs 12 (1): 79.

Spitzer, M., M. Thimm, 1. HermIe, P. Holzmann, K.

A. Kovar, H. Heimann, E. Gouzoulis-Mayfrank,

U. Kischka, and F. Schneider. 1996. Increased

activation of indirect semantic associations

under psilocybin. Biological Psychiatry

39:1055-57.

Strassmann, Rick. 1992. DMT and psilocybin

research. Maps 3 (4): 8-9.

---.1995. University of New Mexico DMT and

psilocybin studies. Maps 5 (3): 14-15.

Troxler, F., F. Seemann, and Albert Hofmann. 1959.

Abwandlungsprodukte von Psilocybin und

Psilocin. Helvetica Chimica Acta 42 (226):

2073-103.

Vollenweider, Franz. 1996. Perspektiven der

BewuBtseinsforschung mit Halluzinogenen. In

Maria Sabina-Botin der heiligen Pilze, ed. Roger

Liggenstorfer and Christian R~itsch, 203-10.

Solothurn: Nachtschatten Verlag.</td>
</tr>

</table>

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2013-01-13T17:43:33Z

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== Drug Knowledge ==

:✔ = Good Page

* Depressants
** [[Cannabis]]
** [[Alcohol]]
** [[Benzodiazepines]]
** [[GHB]]

* Opioids
** [[Heroin]]
** [[Poppy extracts]]
** [[Oxycodone]]
** [[Fentanyl]]

* [[Psychedelics]]
** [[LSD]]
** [[DMT]]
** [[Mushrooms]]
** [[Salvia]]
** [[2C-X|2C-X series]]
** [[NBOMe|NBOMe series]]

* [[Stimulants]]
** [[Street amphetamine]]
** [[Methamphetamine]]
** [[Adderal]]
** [[MDMA]]

* '''[[Dissociatives]]''' ✔
** [[Ketamine]]
** [[DXM]]
** [[MXE]]
** [[Nitrous]]

* [[Deliriants]]
** [[Scopolamine]]
** [[Diphenhydramine]]

</td>

<td valign=top width=15%>
== Entheogens ==
* [[Gold Pepper]]
* [[Kougoed]]
* [[Scopolia]]
* [[Cup of Gold]]
* [[Ska Maria Pastora]]
* [[Sassafras Tree]]

==[[Compounds]]==
* [[B-Carbolines]]
* [[THC]]
* [[Tropane Alkaloids]]
* [[Psilocybin/Psilocin]]
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Tropane Alkaloids

2013-01-13T17:39:01Z

205.56.181.196:

<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">

<tr>
<td valign="top" width="50%">Other Names

Tropanalkaloide, tropanes, tropeine

Tropane alkaloids are esters of tropanal combined

with various acids. They occur primarily in

nightshades (Solanaceae), especially the psychoactive

ones. The most important psychoactive

tropane alkaloids are atropine, scopolamine, and

hyoscyamine. These substances are "quickly

absorbed through the mucous membranes but

also through the intact skin" (Roth et al. 1994,

944*). For this reason, plant preparations in the

form of ointments with these tropane alkaloids

can induce psychoactive effects (cf. Datura

innoxia, witches' ointments). Atropine, scopolamine,

and hyoscyamine are found in the genera

Atropa, Brugmansia, Datum, Hyoscyamus, Iochroma,

]uanulloa, Mandragora, Solandra, and Scopolia.

The psychoactive tropane alkaloid hyoscyamine

(cf. Hyoscyamus niger) occurs in the following

nightshades in concentrations that appear to make

them useful for psychoactive purposes (Festi 1995,

132 f.*): Anthoceris littorea Labill. (herbage),

Crenedium spinescens Haegi (leaves), Cyphanthera

anthocercidea (Ev. Muel!.) Haegi (leaves),

Mandragora caulescens C.B. Clarke (entire plant;

cf. Mandragora spp.), Physochlaina praealta

(Decne.) Miers (entire plant), and Scopolia lurida

Dunal (roots; cf. Scopolia carniolica). As a plant

dries, the hyoscyamine it contains is usually

transformed into its analog scopolamine. The

profile of effects of hyoscyamine is essentially the

same as that of scopolamine.

Tropanes and cocaine are chemically related

and can under certain conditions elicit similar

pharmacological effects (Sauerwein et al. 1993).

The tropane alkaloid 2-tropanone is a metabolic

product of cocaine. Tropane alkaloids occur in

most if not all Erythroxylum species (AI-Said et al.

1989). The bark of Erythroxylum zambesiacum N.

Robson has been found to contain various

tropanes (Christen et al. 1993). The root bark of

Erythroxylum hypericifolium Lam., a species indigenous

to Mauritius that is used in folk medicine

to treat kidney problems, contains large amounts

of hygrine as well as other tropanes (e.g., cuscohygrine)

(AI-Said et al. 1989). Both hygrine and

cuscohygrine are also found in the leaves and bark

of the two coca species Erythroxylum coca and

Erythroxylum novogranatense (AI-Said et al. 1989,

672). The leaves of the Southeast Asian species

Erythroxylum cuneatum (Wall.) Kurz, which is

used in Malaysia as a tonic, were found to contain as their primary alkaloid (±)-3<X,613-dibenzoyloxytropane;

another major constituent in the leaves is

nicotine. The main alkaloid in the leaves of

another ethnomedicinally useful Southeast Asian

species, Erythroxylum ecarinatum Burck., is tropacacaine.

The root bark of the Australian species

Erythroxylum australe Ev. Muell. also contain

numerous tropanes (meteloidine) (EI-Imam et al.

1988).

Tropane alkaloids also appear to be present in

the Proteaceae Family, e.g., in the species Knightia

strobolina (EI-Imam et aL 1988:2182). In Australia,

several members of the genera Hakea and Banksia

are used to produce wine.

The recent discovery of tropane alkaloids

(tropine, tropinone, cuscohygrine, hygrine) in

field bindweed (Convolvulus arvensis 1.; cf. Convolvulus

tricolor) is very interesting; the species

also contains ergot alkaloids (Todd et al. 1995).

Tropane alkaloids have also been found in the

hedge bindweed Calystegia sepium (1.) R. Br. [syn.

Convolvulus sepium] (Goldmann et al. 1990).</td>
<td valign="top" width="53%">Literature

See also the entries for atropine and scopolamine.

Bauer, Eduard. 1919. Studium aber die Bedeutung der

Alkaloide in pharmakognostisch wichtigen

Solanaceen, besonders in Atropa Belladonna und

Datura Stramonium. Bern: Hallwag.

Christen, P., M. F. Roberts, J. D. Phillipson, and W. C.

Evans. 1993. Recent aspects of tropane alkaloid

biosynthesis in Erythroxylum zambesiacum stem

bark. Planta Medica 59 supp!.: A583-84.

Goldmann, Arlette, Marie-Louise Milat, Paul-Henri

Ducrot, Jean-Yves Lallemand, Monique Maille,

Andree Lepingle, Isabelle Charpin, and David

Tepfer. 1990. Tropane derivates from Calistegia

sepium. Phytochemistry 29 (7): 2125-27.

Imam, Yahia M. A. e1-, William C. Evans, and

Raymond J. Grout. 1988. Alkaloids of

Erythroxylum cuneatum, E. ecarinatum and E.

australe. Phytochemistry 27 (7): 2181-84.

Said, Mansour S. al-, William C. Evans, and

Raymond J. Grout. 1989. Alkaloids of

Erythroxylum hypericifolium stem bark.

Phytochemistry 28 (2): 671-73.

Sauerwein, M., F. Sporer, and M. Wink. 1993.

Allelochemical properties of derivatives from

tropane and ecgonine. Planta Medica 59 suppL:

A662

Todd, G. Fred, F. R. Stermitz, P. Schultheiss, A. P.

Traub-Dargatz, and J. Traub-Dargatz. 1995.

Tropane alkaloids and toxicity of Convolvulus

arvensis. Phytochemistry 39:301-3.

Xiao, P., and 1. Y. He. 1983. Ethnopharmacologic

investigation on tropane-containing drugs in

Chinese Solanaceous plants. Journal of

Ethnopharmacology 8: 1-18.</td>
</tr>

2013-01-13T17:19:25Z

205.56.181.196:

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== Community ==

=== Radio ===

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=== IRC chat ===

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=== IRC network ===

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=== Nexus ===
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*[[Nexus Wiki Page|Nexus Wiki]]
*[http://www.tripsit.me/network/tripsit-network/features/ Features]
*[http://www.tripsit.me/network/tripsit-network/terms/ Terms & Conditions]

=== Tripsitting ===
* [[Tripsit howto|How to be a good trip sitter]]
* [[Handling bad trips|How to handle a bad trip]]

</td>

<td valign=top width=15% bgcolor=#f1f1f1>
== Drug Knowledge ==

:✔ = Good Page

* Depressants
** [[Cannabis]]
** [[Alcohol]]
** [[Benzodiazepines]]
** [[GHB]]

* Opioids
** [[Heroin]]
** [[Poppy extracts]]
** [[Oxycodone]]
** [[Fentanyl]]

* [[Psychedelics]]
** [[LSD]]
** [[DMT]]
** [[Mushrooms]]
** [[Salvia]]
** [[2C-X|2C-X series]]
** [[NBOMe|NBOMe series]]

* [[Stimulants]]
** [[Street amphetamine]]
** [[Methamphetamine]]
** [[Adderal]]
** [[MDMA]]

* '''[[Dissociatives]]''' ✔
** [[Ketamine]]
** [[DXM]]
** [[MXE]]
** [[Nitrous]]

* [[Deliriants]]
** [[Scopolamine]]
** [[Diphenhydramine]]

*[[Compounds]]
** [[B-Carbolines]]

</td>

<td valign=top width=15%>
== Entheogens ==
* [[Gold Pepper]]
* [[Kougoed]]
* [[Scopolia]]
</td>

<td valign=top width=33%>
== Important Pages ==
* [[To do list]]
* [[Admin Daily Digest]]
* [[List of people|List of staff and their roles]]

== Philosophy and Spirituality ==
* [[Tree Idea]]
* [[DILD]]
* [[Disso Theory]]
* [[Dimensions]]
* [[MBTI mind reading theory]]
* [[Egg Theory]]
</td>

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</table>

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