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Tetrahydrocannabinol

From Academic Kids

Tetrahydrocannabinol (THC)
Chemical name(-)-(6aR,10aR)-6,6,9-trimethyl-
3-pentyl-6a,7,8,10a-tetrahydro-
6H-benzo[c]chromen-1-ol
Chemical formulaC21H30O2
Molecular mass314.46 g/mol
Boiling point200 °C
Solubility2.8 g/l (water, 23 °C)
CAS number1972-08-3
SMILESCCCCCC(C=C1O)=CC2=C1[C@]3([H])
[C@](C(C)(C)O2)([H])CCC(C)=C3
Missing image
THC_structure.png
Chemical structure of tetrahydrocannabinol


Tetrahydrocannabinol, also known as THC, Δ9-THC, Δ9-tetrahydrocannabinol (delta-9-tetrahydrocannabinol), Δ1-tetrahydrocannabinol (using an older numbering scheme), or dronabinol, is the main psychoactive substance found in the hemp plant Cannabis sativa. It was isolated by Raphael Mechoulam and Yechiel Gaoni from the Weizmann Institute in Rehovot, Israel in 1964. In pure form it is glassy solid when cold and becomes viscous and sticky if warmed. THC has a very low solubility in water, but a good solubility in most organic solvents like ethanol or hexane.

Contents

Pharmacology

Its pharmacological actions are the result of its binding to specific cannabinoid receptors located in the brain and throughout the body. Since cannabinoids are not naturally produced in the human body, the search began for the endogenous substance that normally binds to this receptors, the so-called natural ligand, leading to the eventual discovery of anandamide and some related compounds.

Effects include relaxation, euphoria, altered space-time perception, alteration of visual, auditory, and olfactory senses, disorientation, and appetite stimulation.

Toxicity

THC has a LD50 value of 1270 mg/kg (male rats), 730 mg/kg (female rats) orally (administered dissolved in sesame oil). Studies of the distribution of the receptors in the brain explain why toxicity of THC is so low (i.e., the LD50 of the compound is so large): parts of the brain that control vital functions such as respiration do not have many receptors, so are relatively unaffected even by doses larger than could ever be ingested under any normal conditions.

Research

A number of studies indicate medical benefits for cancer and AIDS patients by increasing appetite and decreasing nausea, blocking the spread of some cancer-causing Herpes simplex viruses. It has been shown to assist some glaucoma patients by reducing pressure within the eye, and is used, in the form of cannabis by a number of multiple sclerosis patients for relieving spasm. Other disputed studies indicate a variety of negative effects associated with constant, long-term use, including memory loss, depression and loss of motivation, though anecdotal evidence gives a very different picture. The long-term effects of THC on humans are disputed, and the issue is politicized because of its status as an illegal drug.

Synthetic THC

Synthetic THC, also known under the substance name dronabinol, is available as a prescription drug (e.g. under the trade name Marinol) in several countries including the USA, The Netherlands, and Germany. In the United States, Marinol is a schedule III drug, available by prescription, considered to be non-narcotic and to have a low risk of physical or mental dependence. Efforts to get cannabis rescheduled as analogous to Marinol have not succeeded thusfar.

In July 2005 Canadian authorities approved the marketing of Sativex, a mouth spray for multiple sclerosis to alleviate pain. Sativex contains tetrahydrocannabinol together with cannabidiol. It is marketed in Canada by GW Pharmaceuticals, being the first cannabis-based drug in the world.

See also

External links

  • Scientific American (http://www.sciam.com/article.cfm?articleID=000A844E-8FBE-119B-8EA483414B7FFE9F&ref=sciam&chanID=sa004) Marijuana research
  • THC-pharm (http://www.thc-pharm.de), a German producer of THC for pharmacies.
  • Erowid (http://www.erowid.org/plants/cannabis/cannabis_info2.shtml) Compounds found in Cannabis sativa.

Template:Cannabinoidsde:Tetrahydrocannabinol es:Tetrahidrocannabinol fr:Tétrahydrocannabinol nl:Tetrahydrocannabinol pl:Tetrahydrokannabinol sv:Tetrahydrocannabinol

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