Tetrahydrocannabinal
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| Clinical data | |
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| Trade names | Marinol |
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| Dependence liability |
8–10% (Relatively low risk of tolerance) |
| Addiction liability |
Low |
| Routes of administration |
Oral, local/topical, transdermal, sublingual, inhaled |
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| Pharmacokinetic data | |
| Bioavailability | 10–35% (inhalation), 6–20% (oral) |
| Protein binding | 97–99% |
| Metabolism | Mostly hepatic by CYP2C |
| Biological half-life | 1.6–59 h, 25–36 h (orally administered dronabinol) |
| Excretion | 65–80% (feces), 20–35% (urine) as acid metabolites |
| Identifiers | |
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| Synonyms | (6aR,10aR)-delta-9-tetrahydrocannabinol, (−)-trans-Δ⁹-tetrahydrocannabinol |
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| ECHA InfoCard | 100.153.676 |
| Chemical and physical data | |
| Formula | C21H30O2 |
| Molar mass | 314.469 g/mol |
| 3D model (Jmol) | |
| Specific rotation | −152° (ethanol) |
| Boiling point | 155-157°C @ 0.05mmHg, 157-160°C @ 0.05mmHg |
| Solubility in water | 0.0028, (23 °C) mg/mL (20 °C) |
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Tetrahydrocannabinol (THC, dronabinol, trade name Marinol) is the principal psychoactive constituent (or cannabinoid) of cannabis. The pharmaceutical formulation dronabinol, is available by prescription in the U.S. and Canada. It can be a clear, amber or gold colored glassy solid when cold, which becomes viscous and sticky if warmed.
Like most pharmacologically-active secondary metabolites of plants, THC in Cannabis is assumed to be involved in self-defense, perhaps against herbivores. THC also possesses high UV-B (280–315 nm) absorption properties, which, it has been speculated, could protect the plant from harmful UV radiation exposure.
THC, along with its double bond isomers and their stereoisomers, is one of only three cannabinoids scheduled by the UN Convention on Psychotropic Substances (the other two are dimethylheptylpyran and parahexyl). It was listed under Schedule I in 1971, but reclassified to Schedule II in 1991 following a recommendation from the WHO. Based on subsequent studies, the WHO has recommended the reclassification to the less-stringent Schedule III. Cannabis as a plant is scheduled by the Single Convention on Narcotic Drugs (Schedule I and IV). It is specifically still listed under Schedule I by US federal law under the Controlled Substances Act signed by the US Congress in 1970.
Dronabinol is the INN for a pure isomer of THC, (–)-trans-Δ⁹-tetrahydrocannabinol, which is the main isomer found in cannabis. It is used to treat anorexia in people with HIV/AIDS as well as for refractory nausea and vomiting in people undergoing chemotherapy. It is safe and effective for these uses.
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Wikipedia