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Tetrahydrocannabinol

Tetrahydrocannabinol (THC)
Systematic (IUPAC) name
(−)-(6aR,10aR)-6,6,9-trimethyl-
3-pentyl-6a,7,8,10a-tetrahydro-
6H-benzo[c]chromen-1-ol
Identifiers
CAS number1972-08-3
ATC codeA04AD10
PubChem16078
DrugBankAPRD00571
ChemSpider15266
Chemical data
FormulaC21H30O2 
Mol. mass314.45
SMILESeMolecules & PubChem
SynonymsDronabinol
Physical data
Boiling point200 °C (392 °F) 0.02mmHg
Solubility in water2.8 mg/L[1] (23 °C) mg/mL (20 °C)
Spec. rot-152° (ethanol)
Pharmacokinetic data
Bioavailability10-35% (inhalation), 6-20% (oral)[2]
Protein binding95-99%[2]
Metabolismmostly hepatic by CYP2C[2]
Half life1.6-59 hours [2], 25-36 hours (orally administered Dronabinol)
Excretion65-80% (feces), 20-35% (urine) as acid metabolites[2]
Therapeutic considerations
Pregnancy cat.

C

Legal status
Dependence LiabilitySchedule I and III (US)
Routes ?
3D rendering of the THC molecule.

Tetrahydrocannabinol (IPA: /ˌtɛtrəˌhaɪdrəkəˈnæbənɒl/, tet-rə-HYE-drə-kə-NAB-ə-nol), also known as THC, Δ9-THC, Δ9-tetrahydrocannabinol (delta-9-tetrahydrocannabinol), Δ1-tetrahydrocannabinol (using an older chemical nomenclature), or dronabinol, is the main psychoactive substance found in the Cannabis plant. It was isolated by Raphael Mechoulam, Yechiel Gaoni, and Habib Edery from the Weizmann Institute of Science in Rehovot, Israel in 1964.[3][4][5] In pure form, it is a glassy solid when cold and becomes viscous and sticky if warmed. An aromatic terpenoid, THC has a very low solubility in water, but good solubility in most organic solvents such as butane or hexane. Like most pharmacologically-active secondary metabolites of plants, THC in Cannabis is assumed to be involved in self-defense, perhaps against herbivores.[6] 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.[citation needed]

Dronabinol is the International Nonproprietary Name (INN) for a pure isomer of THC, (-)-trans-Δ9-tetrahydrocannabinol, that is, the main isomer in Cannabis.[7] It is sold as Marinol (a registered trademark of Solvay Pharmaceuticals). Dronabinol is also marketed, sold, and distributed by PAR Pharmaceutical Companies under the terms of a license and distribution agreement with SVC pharma LP, an affiliate of Rhodes Technologies.

 

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