Tetrahydrocannabinol

Tetrahydrocannabinol
INN: Dronabinol
Clinical data
Trade names	Marinol, Syndros
Other names	(6aR,10aR)-delta-9-Tetrahydrocannabinol; (−)-trans-Δ9-tetrahydrocannabinol
License data	US FDA: Dronabinol;
Dependence; liability	Physical: Low ; Psychological: Low–moderate
Addiction; liability	Relatively low: 9%
Routes of; administration	By mouth, transdermal, sublingual, inhalation
Drug class	Cannabinoid
ATC code	A04AD10 (WHO) ;
Legal status
Legal status	AU: Unscheduled: ACT, Schedule 8 (Controlled Drug); BR: Dronabinol: A3; THC <30mg/ml: A3; others: F2 (prohibited).; CA: Unscheduled; DE: Dronabinol: Anlage III, Δ9-THC: II, other isomers and their stereochemical variants: I. (Does not apply to THC as part of cannabis, which is regulated separately, see Cannabis (drug)); UK: Class B; US: Schedule II as Syndros, Schedule III as Marinol, Schedule I as Δ9-THC in pure form; UN: Psychotropic Schedule I /II; In general Rx-only;
Pharmacokinetic data
Bioavailability	Oral: 6–20%; Inhalation: 10–35%;
Protein binding	97–99%
Metabolism	Mostly hepatic by CYP2C
Elimination half-life	1.6–59 h, 25–36 h (orally administered dronabinol)
Excretion	65–80% (feces); 20–35% (urine) as acid metabolites;
Identifiers
	IUPAC name (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol;
CAS Number	1972-08-3 ;
PubChem CID	16078;
IUPHAR/BPS	2424;
DrugBank	DB00470 ;
ChemSpider	15266 ;
UNII	7J8897W37S;
KEGG	D00306 ;
ChEBI	CHEBI:66964 ;
ChEMBL	ChEMBL465 ;
CompTox Dashboard (EPA)	DTXSID6021327 ;
ECHA InfoCard	100.153.676
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image;
Specific rotation	−152° (ethanol)
Boiling point	155–157 °C (311–315 °F) 0.05mmHg, 157–160°C @ 0.05mmHg
Solubility in water	0.0028 mg/mL (23 °C)
	SMILES CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C=C(CC3)C)(C)C)O;
	InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1 ; Key:CYQFCXCEBYINGO-IAGOWNOFSA-N ;
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Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of Cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C₂₁H₃₀O₂) describes multiple isomers, the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans-Δ⁹-tetrahydrocannabinol. It is a colorless oil.