11-Hydroxy-THC

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Image:11-OH-THC.svg
11-Hydroxy-THC
Systematic (IUPAC) name
6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl- 6H-Dibenzo[b,d]pyran-9-methanol
Identifiers
CAS number	36557-05-8
ATC code	?
PubChem	644022
Chemical data
Formula	C21H30O3
Mol. mass	330.461 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-THC) is the main active metabolite of THC which is formed in the body after cannabis is smoked^[1]. 11-hydroxy-THC has been shown to be active in its own right^[2], but the effects produced are not necessarily identical to those of THC^[3]; it is plausible that the biphasic action of cannabis might be explained by the action of the active metabolite of THC rather than by other compounds present in the plant such as cannabidiol, so that 11-hydroxy-THC might be responsible for causing certain effects such as sleepiness and increased appetite which are characteristically delayed and occur as the initial "high" is wearing off.

11-hydroxy-THC is subsequently metabolised further to 11-carboxy-THC, which is not psychoactive but may still play a role in the analgesic and anti-inflammatory effects of cannabis.

References

1. ^ Johnson, J.R.; T.A. Jennison, M.A. Peat, R.L. Foltz (September-October 1984). "Stability of delta 9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC in blood and plasma.". Journal of Analytical Toxicology 8 (5): 202-204.
2. ^ Turkanis, S.A.; R. Karler (July 1988). "Changes in neurotransmitter release at a neuromuscular junction of the lobster caused by cannabinoids". Neuropharmacology 27 (7): 737-742.
3. ^ Hollister, L.E.; H.K. Gillespie (December 1975). "Action of delta-9-tetrahydrocannabinol. An approach to the active metabolite hypothesis". Clinical Pharmacology and Therapeutics 18 (6): 714-719.

v • d • e Cannabinoids
Plant cannabinoids	CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • THCV
Cannabinoid metabolites	11-Hydroxy-THC • 11-nor-9-Carboxy-THC
Endogenous cannabinoids	Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)
Synthetic cannabinoid agonists	Classical cannabinoids (Dibenzopyrans) A-41988 • Ajulemic acid • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-938 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Dexanabinol (HU-211) • DMHP • Dronabinol • HU-210 • JWH-051 • JWH-133 • JWH-139 • L-759,633 • L-759,656 • Levonantradol • Nabilone • Nabitan • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • Parahexyl • THC-O-acetate • THC-O-phosphate Nonclassical cannabinoids CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene Aminoalkylindoles AM-630 • AM-1241 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-200 • L-768,242 • Pravadoline • WIN 55,212-2 Aminoalkylpyrroles JWH-030 • JWH-147 • JWH-307 Eicosanoids AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861 Others BAY 38-7271 • BAY 59-3074 • JWH-171 • O-2220
Endocannabinoid activity enhancers	AM-404 • N-arachidonoyl-serotonin • O-1624 • URB-597 • URB-754
Cannabinoid antagonists and inverse agonists	AM-251 • AM-281 • AM-630 • BML-190 • JTE-907 • LY-320,135 • NESS-0327 • O-1184 • O-2050 • O-2654 • Rimonabant • SLV-319 • SR-144,528 • Surinabant • Taranabant • VCHSR

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .