Tetrahydrocannabinol

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)[3]
Protein binding97–99%[3][4][5]
MetabolismMostly hepatic by CYP2C[3]
Elimination half-life1.6–59 h,[3] 25–36 h (orally administered dronabinol)
Excretion65–80% (feces), 20–35% (urine) as acid metabolites[3]
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,[6] 157–160°C @ 0.05mmHg[7]
Solubility in water0.0028 mg/mL (23 °C)[8]
  • 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
 ☒NcheckY (what is this?)  (verify)

Tetrahydrocannabinol (THC) is a terpenoid found in cannabis.[9] 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,[10] the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans9-tetrahydrocannabinol. It is a colorless oil.

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 – Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ "Marinol" (PDF). Food and Drug Administration. Archived from the original (PDF) on 2014-05-13. Retrieved 2014-03-14.
  3. ^ a b c d e Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics. 42 (4): 327–60. doi:10.2165/00003088-200342040-00003. PMID 12648025. S2CID 25623600.
  4. ^ The Royal Pharmaceutical Society of Great Britain (2006). "Cannabis". In Sweetman SC (ed.). Martindale: The Complete Drug Reference: Single User (35th ed.). Pharmaceutical Press. ISBN 978-0-85369-703-9.[page needed]
  5. ^ "Tetrahydrocannabinol – Compound Summary". National Center for Biotechnology Information. PubChem. Archived from the original on 12 January 2014. Retrieved 12 January 2014. Dronabinol has a large apparent volume of distribution, approximately 10 L/kg, because of its lipid solubility. The plasma protein binding of dronabinol and its metabolites is approximately 97%.
  6. ^ Gaoni Y, Mechoulam R (April 1964). "Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish". Journal of the American Chemical Society. 86 (8): 1646–47. doi:10.1021/ja01062a046.
  7. ^ Adams R, Cain CK, McPhee WD, Wearn RB (August 1941). "Structure of Cannabidiol. XII. Isomerization to Tetrahydrocannabinols". Journal of the American Chemical Society. 63 (8): 2209–13. doi:10.1021/ja01853a052.
  8. ^ Cite error: The named reference Garrett1974 was invoked but never defined (see the help page).
  9. ^ Pichersky E, Raguso RA (November 2018). "Why do plants produce so many terpenoid compounds?". The New Phytologist. 220 (3): 692–702. doi:10.1111/nph.14178. hdl:2027.42/146372. PMID 27604856.
  10. ^ "THC Chemistry by Alexander Shulgin - January 21, 1995". www.druglibrary.org. Archived from the original on 2020-11-12. Retrieved 2020-11-12.