Tetrahydrocannabinol

Tetrahydrocannabinol (Wikipedia)

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. Its chemical formula C21H30O2 includes compounds, the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans9-tetrahydrocannabinol. It is a colorless oil.

Tetrahydrocannabinol
INN: dronabinol
Clinical data
Trade namesMarinol, Syndros
Other names(6aR,10aR)-delta-9-Tetrahydrocannabinol; (−)-trans9-Tetrahydrocannabinol; THC
License data
Dependence
liability
Physical: Low
Psychological: Low–moderate
Addiction
liability
Relatively low: 9%
Routes of
administration
Oral, local/topical, transdermal, sublingual, inhaled
Drug classCannabinoid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability10–35% (inhalation), 6–20% (oral)
Protein binding97–99%
MetabolismMostly hepatic by CYP2C
Elimination half-life1.6–59 h, 25–36 h (orally administered dronabinol)
Excretion65–80% (feces), 20–35% (urine) as acid metabolites
Identifiers
  • (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.153.676 Edit this at Wikidata
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
Specific rotation−152° (ethanol)
Boiling point155–157 °C (311–315 °F) 0.05mmHg, 157–160°C @ 0.05mmHg
Solubility in water0.0028 mg/mL (23 °C)
  • CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C=C(CC3)C)(C)C)O
  • 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 checkY
  • Key:CYQFCXCEBYINGO-IAGOWNOFSA-N checkY
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