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3'-Hydroxy-THC

From Wikipedia, the free encyclopedia
Minor metabolite of THC
Pharmaceutical compound
3'-Hydroxy-THC
Identifiers
  • (6aR,10aR)-3-[(3S)-3-hydroxypentyl]-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChemCID
ChemSpider
Chemical and physical data
FormulaC21H30O3
Molar mass330.468 g·mol−1
3D model (JSmol)
  • CC[C@H](O)CCc1cc2OC(C)(C)[C@@H]3CCC(C)=C[C@H]3c2c(O)c1
  • InChI=1S/C21H30O3/c1-5-15(22)8-7-14-11-18(23)20-16-10-13(2)6-9-17(16)21(3,4)24-19(20)12-14/h10-12,15-17,22-23H,5-9H2,1-4H3/t15?,16-,17-/m1/s1
  • Key:GWSPOZKXWMVVEN-YJEKIOLLSA-N

3'-Hydroxy-THC (3'-OH-Δ9-THC) is a minoractive metabolite ofTHC, the main psychoactive component ofcannabis. 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, theS 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 as11-Hydroxy-THC and8,11-Dihydroxy-THC, it is thought to contribute to the overall pharmacological profile of cannabis.[1][2][3][4][5]

See also

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References

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  1. ^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.
  2. ^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.
  3. ^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.
  4. ^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.
  5. ^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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