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

Revision as of 09:21, 11 March 2015

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,


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


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 (dopamineA neurotransmitter associated with movement, attention, learning, and the brain’s pleasure and reward system., N-methyldopamine,

adrenaline, noradrenaline) and tryptamines (serotoninA monoamine neurotransmitter, biochemically derived from tryptophan, that is primarily found in the gastrointestinal (GI) tract, platelets, and central nervous system (CNS) of humans and animals. It is a well-known contributor to feelings of well-being.,

N-methyl-serotoninA monoamine neurotransmitter, biochemically derived from tryptophan, that is primarily found in the gastrointestinal (GI) tract, platelets, and central nervous system (CNS) of humans and animals. It is a well-known contributor to feelings of well-being., 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,


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).
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*).


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:


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.

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