Tetrahydrocannabinol

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	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.^[9] 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,^[10] the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans-Δ⁹-tetrahydrocannabinol. It is a colorless oil.

^ 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.
^ "Marinol" (PDF). Food and Drug Administration. Archived from the original (PDF) on 2014-05-13. Retrieved 2014-03-14.
^ ^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.
^ 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]}
^ "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%.
^ 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. Bibcode:1964JAChS..86.1646G. doi:10.1021/ja01062a046.
^ 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. Bibcode:1941JAChS..63.2209A. doi:10.1021/ja01853a052.
^ Cite error: The named reference Garrett1974 was invoked but never defined (see the help page).
^ Pichersky E, Raguso RA (November 2018). "Why do plants produce so many terpenoid compounds?". The New Phytologist. 220 (3): 692–702. Bibcode:2018NewPh.220..692P. doi:10.1111/nph.14178. hdl:2027.42/146372. PMID 27604856.
^ "THC Chemistry by Alexander Shulgin - January 21, 1995". www.druglibrary.org. Archived from the original on 2020-11-12. Retrieved 2020-11-12.

[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.

[pmid12648025-3] Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics. 42 (4): 327–60. doi:10.2165/00003088-200342040-00003. PMID 12648025. S2CID 25623600.

[Martindale-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. Bibcode:1964JAChS..86.1646G. 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. Bibcode:1941JAChS..63.2209A. doi:10.1021/ja01853a052.

[Garrett1974-8] 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. Bibcode:2018NewPh.220..692P. 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.

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