3'-히드록시-THC

3'-Hydroxy-THC
3'-히드록시-THC
3'-OH-THC structure.png
식별자
  • (6aR,10aR)-3-[(3S)-3-하이드록시펜틸]-6,6,9-트리메틸-6a,7,8,10a-테트라하이드로벤조[c]크로멘-1-올
펍켐 CID
켐스파이더
화학 및 물리적 데이터
공식C21H30O3
어금질량330.468 g·1998−1
3D 모델(JSmol)
  • CC[C@H](O)CC1CC2OC(C)[C@H]3CC(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
  • 키:GWSPOZKXWMVEN-YJEKIOLLSA-N

3'-히드록시-THC(3'-OH-Δ-THC9)는 대마초의 주요 정신 활성 성분인 THC의 소 활성 대사물이다. 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, 대마초의 전반적인 약리학적 프로파일에 기여할 것으로 생각된다.[1][2][3][4][5]

참고 항목

참조

  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.
  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.
  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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