Tetrahydrocannabinol

Tetrahydrocannabinol (THC) is a terpenoid found in cannabis. It is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Its chemical formula C₂₁H₃₀O₂ includes compounds, the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans-Δ⁹-tetrahydrocannabinol. It is a colorless oil.

Tetrahydrocannabinol
INN: dronabinol

Clinical data
Trade names	Marinol, Syndros
Other names	(6aR,10aR)-delta-9-Tetrahydrocannabinol; (−)-trans-Δ9-Tetrahydrocannabinol; THC
License data	US FDA: Dronabinol
Dependence liability	Physical: Low Psychological: Low–moderate
Addiction liability	Relatively low: 9%
Routes of administration	Oral, local/topical, transdermal, sublingual, inhaled
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, and Schedule III as Marinol UN: Psychotropic Schedule I /II
Pharmacokinetic data
Bioavailability	10–35% (inhalation), 6–20% (oral)
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 Y
PubChem CID	16078
IUPHAR/BPS	2424
DrugBank	DB00470 Y
ChemSpider	15266 Y
UNII	7J8897W37S
KEGG	D00306 Y
ChEBI	CHEBI:66964 N
ChEMBL	ChEMBL465 Y
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 Y Key:CYQFCXCEBYINGO-IAGOWNOFSA-N Y
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