Misplaced Pages

This is an old revision of this page, as edited by Sativa Inflorescence (talk | contribs) at 02:22, 5 January 2023. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

11-Hydroxy-THC

Clinical data
Drug class	Cannabinoid
Legal status
Legal status	UK: Class B
Identifiers
IUPAC name (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzochromen-1-ol
CAS Number	36557-05-8
PubChem CID	37482
ChemSpider	34385
UNII	9VY04N5SLB
CompTox Dashboard (EPA)	DTXSID50190061
ECHA InfoCard	100.164.583
Chemical and physical data
Formula	C21H30O3
Molar mass	330.468 g·mol
3D model (JSmol)	Interactive image
SMILES Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC
InChI InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3 Key:YCBKSSAWEUDACY-UHFFFAOYSA-N
(what is this?)  (verify)

11-Hydroxy-Δ-tetrahydrocannabinol (11-OH-Δ-THC, alternatively numbered as 7-OH-Δ-THC), usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC).

After cannabis consumption, THC is metabolized inside the body by cytochrome P450 enzymes such as CYP2C9 and CYP3A4 into 11-hydroxy-THC and then further metabolized by the dehydrogenase and CYP2C9 enzyme to form 11-nor-9-carboxy-THC (THC-COOH) which is inactive at the CB1 receptors; and further glucuronidated to form 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-THC-COOH-glu) where it is excreted in both feces and urine. Both compounds, along with THC, can be assayed in drug tests.

THC administered orally results in higher 11-OH-THC plasma concentration compared to smoking.

See also

• 3'-Hydroxy-THC
• 7-Hydroxycannabidiol
• 8,11-Dihydroxytetrahydrocannabinol
• 11-Hydroxy-Delta-8-THC
• 11-OH-CBN
• Cannabis edible

References

1. ^ Kraemer T, Paul LD (August 2007). "Bioanalytical procedures for determination of drugs of abuse in blood". Analytical and Bioanalytical Chemistry. 388 (7): 1415–1435. doi:10.1007/s00216-007-1271-6. PMID 17468860. S2CID 32917584.
2. ^ Huestis MA (2005). "Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol". Handbook of Experimental Pharmacology. 168 (168): 657–690. doi:10.1007/3-540-26573-2_23. ISBN 3-540-22565-X. PMID 16596792.
3. Stout SM, Cimino NM (February 2014). "Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review". Drug Metabolism Reviews. 46 (1): 86–95. doi:10.3109/03602532.2013.849268. PMID 24160757. S2CID 29133059.
4. Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics. 42 (4): 327–360. doi:10.2165/00003088-200342040-00003. PMID 12648025. S2CID 25623600.
5. Pertwee, Robert (2005). Cannabinoids Handbook of Experimental Pharmacology volume 168. Germany: Springer. p. 667. ISBN 3-540-22565-X.

• Cannabinoids
• Benzochromenes
• Primary alcohols
• Phenols
• Prodrugs