3'-Hydroxy-THC
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Minor metabolite of THC
Pharmaceutical compound
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| Formula | C21H30O3 |
| Molar mass | 330.468 g·mol−1 |
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3'-Hydroxy-THC (3'-OH-Δ9-THC) is a minor active metabolite of THC, the main psychoactive component of cannabis. It is one of a number of metabolites of THC hydroxylated on the pentyl side chain, but while the other side-chain hydroxyl isomers are much weaker or inactive, the S enantiomer of 3'-OH-THC is several times more potent than THC itself, and while it is produced in smaller amounts than other active metabolites such as 11-Hydroxy-THC and 8,11-Dihydroxy-THC, it is thought to contribute to the overall pharmacological profile of cannabis.[1] [2] [3] [4] [5]
See also
[edit ]References
[edit ]- ^ Widman M, Nordqvist M, Dollery CT, Briant RH (November 1975). "Metabolism of delta1-tetrahydrocannabinol by the isolated perfused dog lung. Comparison with in vitro liver metabolism". The Journal of Pharmacy and Pharmacology. 27 (11): 842–8. doi:10.1111/j.2042-7158.1975.tb10227.x. PMID 1493. S2CID 25711286.
- ^ Agurell S, Binder M, Fonseka K, Lindgren JE, Leander K, Martin B, et al. (1976). "Cannabinoids: Metabolites hydroxylated in the pentyl side chain.". In Nahas GG, Paton WD, Idänpään-Heikkilä JE (eds.). Marihuana. Berlin, Heidelberg: Springer. pp. 141–157. doi:10.1007/978-3-642-51624-5_12. ISBN 978-3-642-51626-9.
- ^ Handrick GR, Duffley RP, Lambert G, Murphy JG, Dalzell HC, Howes JF, et al. (December 1982). "3'-Hydroxy- and (+/-)-3',11-dihydroxy-delta 9-tetrahydrocannabinol: biologically active metabolites of delta 9-tetrahydrocannabinol". Journal of Medicinal Chemistry. 25 (12): 1447–50. doi:10.1021/jm00354a011. PMID 6296389.
- ^ Martin BR, Kallman MJ, Kaempf GF, Harris LS, Dewey WL, Razdan RK (July 1984). "Pharmacological potency of R- and S-3'-hydroxy-delta 9-tetrahydrocannabinol: additional structural requirement for cannabinoid activity". Pharmacology, Biochemistry, and Behavior. 21 (1): 61–5. doi:10.1016/0091-3057(84)90131-x. PMID 6087379. S2CID 45091289.
- ^ Huestis MA (August 2007). "Human cannabinoid pharmacokinetics". Chemistry & Biodiversity. 4 (8): 1770–804. doi:10.1002/cbdv.200790152. PMC 2689518 . PMID 17712819.
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