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

Ll9-tetrahydrocannabinol, .1.9-THC, delta-9-THC,

Lll-3,4-trans-tetrahydrocannabinol, tetrahydro-6,6,9

-trimethyl-3-pentyl-6H-di-benzo [b,d]pyran-l-ol,

trans-THC

Substance type: cannabinoid, pyrane derivative,

pyranol derivative

THC is the main active constituent of the three

hemp species Cannabis indica, Cannabis ruderalis,

and Cannabis sativa. THC has not yet been found

in any other plants. The information suggesting

that THC is pyrochemically synthesized when

olibanum (the resin of Boswellia sacra) is burned

is contradictory. Similarly, no trace of THC or its

analogs has yet been found in hops (Humulus

lupulus). THC and its metabolites have been found

in Egyptian mummies (Balabanova et al. 1992).

While trans-THC is psychoactive, the isomer

cis-THC is not (Kempfert 1977):

The effective dosage of THe when smoked is

between 2 and 22 mg and when taken orally is

between 20 and 90 mg. When smoked under

normal conditions, 16 to 19% of the THe is

consumed and the rest is pyrolized. No lethal

dosage is known. However, experiments with

animals indicate that the ratio between an

effective and a lethal dosage can be estimated

to be 4,000 to 40,000. In comparison, this ratio

for alcohol is 4 to 10. (Fromberg 1996,37)

In the blood, THC is transformed into the

active metabolite 11-hydroxy-Ll9-THC. This substance

is absorbed by fatty tissues after about thirty

minutes and is then released back into the blood,

metabolized, and excreted. After only a few days, all

of the substance has been excreted by the body. With

chronic use, 11-hydroxy-THC accumulates in the

fatty tissues and in the liver and can be detected for

a longer period of time (urine tests!; cf. Rippchen

1996).

THC receptors have been discovered both in

the central nervous system and in the peripheral

pathways (Compton 1993; Devane et al. 1989; Matsuda et al. 1990). The THC or cannabinoid

receptor in the nervous system has now been

studied extensively and is very well understood

(Pertwee 1995). Normally, endogenous neurotransmitters

known as anandamides bind to these

receptors (Devane et al. 1992; Devane and Axelrod

1994; Kruszka and Gross 1994). Nerve diseases

(such as multiple sclerosis) can result if the body

does not produce sufficient amounts of anandamides.

If anandamide deficiencies are responsible

for these diseases, it is possible that they could be

successfully treated with THC (Mechoulam et al.

1994).

Anandamide (= arachidonylethanolamide)the

name is derived from the Sanskrit word

ananda, "bliss"-binds to THC receptors in the

brain and is the endogenous THC analog, even

though the inner structures of the two are quite

different. Recently, anandamide has been discovered

in chocolate and cocoa beans (Theobroma

cacao) as well as in red wine (cf. Vitis vinifera)

(Grotenhermen 1996).

Since 1971, cannabis products have been tested

experimentally as medicines for treating alcoholism,

heroin and amphetamine addiction, emotional

disturbances, muscle spasms, and glaucoma.

In 1990, the microbiologist Gerald Lancs of the

University of South Florida discovered that marijuana

kills the herpes virus (AFP announcement

on May 16, 1990), providing scientific validation

of an old Roman remedy for herpes. The

traditional use of hemp products for asthma has

also received scientific support: "THC dilates the

bronchial passages. Like other medicines, it can be

inhaled as an aerosol to treat bronchial asthma

and produces equally positive effects" (Maurer

1989,48).

The medicinal use of THC and its analogs for

the treatment of glaucoma has become an

established practice. No other substance has been

demonstrated to be better tolerated or more

effective than THC (Maurer 1989). A Swiss group

of researchers was able to show that THC relaxes

the muscular cramping associated with central

nervous system spasticity (e.g., due to multiple

sclerosis or spinal cord injury) (Maurer et al.

1990). The researchers found that THC (at a

dosage of 5 mg) produces effects that are similar to those of codeine but more effective and that THC

is also more easily tolerated. There have also been

encouraging attempts to utilize THC in the

clinical treatment of spasticity and the associated

pain (Hagenbach 1996).

The potential applications [of synthetic THC]

range from the treatment of epilepsy, chronic

pain, multiple sclerosis, and lack of appetite to

a reduction in the "addictive pressure"

associated with opiate addiction. (Schmidt

1996,30)

Synthetic THC is better known by the trade

name Marinol. A dosage of 20 to 45 mg of Marinol

induces a "high" that lasts for only sixty to ninety

minutes. Many patients in the United States who

take Marinol complain that the expensive medicine

is ineffective compared to marijuana when

either smoked or eaten (Jack Herer, pers.comm.).

Pharmacological research is now under way to

develop synthetic THC analogs that could be

marketed as medicines. The goal is to isolate the

medically useful properties of THC while removing

the psychoactive ones (Evans 1991). One of the

products that has been synthesized as a result of

this research is the cannabinoid analog HU-210)

chemically known as (-)1l-0H-Ll8-THC-dimethylheptyl.

This substance not only is psychoactive but

is some one hundred to eight hundred times more

potent than natural THC (Ovadia et al. 1995).

However) government health departments and

pharmaceutical companies are more interested in

THC analogs that are devoid of psychoactive

effects. Some critics of this research take a different

position) arguing that the therapeutic effects of

THC are directly related to its psychoactivity.</td>
<td valign="top" width="53%"><strong>Commercial Forms and Regulations</strong>

In principle) THC is an illegal substance throughout

the world (cf. Cannabis indica). However) for

the past several years certain prescription drugs

containing THC have been available in the United

States under the trade names Canasol and Marinol.

Physicians may prescribe these for glaucoma and

cancer patients. In Europe) these drugs can be

obtained only from pharmacies that sell foreign

medicines, and they are extremely expensive.

Recently) there have been efforts in several states in

the United States as well as in several European

nations to make THe and/or Cannabis products

more readily available to patients suffering from a

variety of conditions. There is) however) considerable

resistance to such liberalization efforts. In

spite of the very long history of use of THC and

Cannabis in numerous .cultures and for a wide

variety of purposes (see Ratsch 2001 ) it remains

to be seen whether these substances will ever

become widely accepted and legitimately used.

<strong>Literature</strong>

See also the entries for Cannabis indica and

Cannabis sativa.

Compton, David R, Kenner C. Rice, Brian R.

de Costa, Raj K. Razdan, Lawrence S. Melvin,

M. Ross Johnson) and Billy R Martin. 1993.

Cannabinoid structure-activity relationships:

Correlation of receptor binding and in vivo

activities. The Journal ofPharmacology and

Experimental Therapeutics 265:218-26.

Devane) William A.) and Julius Axelrod. 1994.

Enzymatic synthesis of anandamide) an

endogenous ligand for the cannabinoid receptor,

by brain membranes. Proceedings ofthe National

Academy ofScience, USA 91:6698-701.

Devane, William A., Francis A. Dysarz III, M. Ross

Johnson) Lawrence S. Melvin) and Alynn C.

Howlett. 1988. Determination and

characterization of a cannabinoid receptor in rat

brain. Molecular Pharmacology 34:605-13.

Devane) William A.) Lumir Hanus) Aviva Breuer)

Roger G. Pertwee, Lesley A. Stevenson) Graeme

Griffin) Dan Gibson) Asher Mandelbaum)

Alexander Etinger) and Raphael Mechoulam.

1992. Isolation and structure of a brain

constituent that binds to the cannabinoid

receptor. Science 258:1946-49.

Evans) Fred J. 1991. Cannabinoids: The separation of

central from peripheral effects on a structural

basis. Planta Medica 57 supp!. (1): 60-67.

Fromberg, Erik. 1996. Die Pharmakologie von

Cannabis. In Cannabis, ed. Jurgen Neumeyer)

36-42. [Munich]: Packeispresse Verlag Hans

Schickert.

Grotenhermen) Franjo. 1996. Schokolade) Haschisch

undAnandamide. Hanft 12/96:14-15.

Hagenbach, Ulrike. 1996. Spinale Spastik und

Spasmolyse: 1st die Therapie mit THC eine

unerwartete Bereicherung? In Jahrbuch des

Europiiischen Collegiums fur Bewufltseinsstudien

(1995) 199-207. Berlin: VWB.

Iversen) Leslie 1. 1993. Medical uses of marijuana?

Nature 365:12-13.

Kettenes-van den Bosch, J. J., and C. A. Salemink.

1980. Biological activity of the

tetrahydrocannabinols. Journal of

Ethnopharmacology 2:197-231. (Very good

bibliography.)

Kruszka) Kelly K.) and Richard W. Gross. 1994. The

ATP- and coA-independent synthesis of

arachidonoylethanolamide: A novel mechanism

underlying the synthesis of the endogenous

ligand of the cannabinoid receptor. The Journal of

Biological Chemistry 269 (20): 14345-48.

Matsuda) Lisa A.) Stephen J. Lolait) Michael J.

Brownstein, Alice C. Young, and Tom 1. Bonner.

1991. Structure of a cannabinoid receptor and functional expression of the cloned cDNA.

Nature 346:561-64.

Maurer, Maja. 1989. Therapeutische Aspekte von

Cannabis in der westlichen Medizin. In 3.

Symposion uber psychoaktive Substanzen und

veranderte Bewufltseinszustande in Forschung und

Therapie, ed. M. Schlichting and H. Leuner,

46-49. Gottingen: ECBS.

Maurer, M., V. Henn, A. Dittrich, and A. Hofmann.

1990. Delta-9-tetrahydrocannabinol shows

antispastic and analgesic effects in a single case

double-blind trial. European Archives of

Psychiatry and Clinical Neuroscience 240: 1-4.

Mechoulam, Raphael, Zvi Vogel, and Jacob Barg.

1994. CNS cannabinoid receptors: Role and

therapeutic impl·cations for CNS disorders. CNS

Drugs 2 (4): 255 60.

Mestel, Rosie. 1993. annabis: The brain's other

supplier. New Sc entist7/93:21-23.

Ovadia, H., A. Wohlman, R. Mechoulam, and J.

Weidenfeld. 1995. Characterization of the

hypothermic effect of the synthetic cannabinoid

HU-210 in the rat: Relation to the adrenergic

system and endogenous pyrogens.

Neuropharmacology 34 (2): 175-80.

Pertwee, Roger, ed. 1995. Cannabinoid receptors. New

York: Harcourt Brace Jovanovich.

Rippchen, Ronald, ed. [1996]. Mein Urin gehort mir.

Lorbach: Edition Rauschkunde.

Schmidt, Sebastian. 1996. Die THC-Pille auf Rezept.

Hanfblatt3 (20): 30-31.

Smith, R. Martin, and Kenneth D. Kempfert. 1977.

~.l-3,4-cis-tetrahydrocannabinol in Cannabis

sativa. Phytochemistry 16:1088-89.

Zeeuw, Rokus A. de, and Jaap Wijsbeek. 1972.

Cannabinoids with a propyl side chain in

cannabis: Occurrence and chromatographic

behavior. Science 175:778-79</td>
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THC - Revision history

GrimReaper at 10:46, 11 March 2015