3'-Hydroxy-THC

3'-Hydroxy-THC
Identifiers
	IUPAC name (6aR,10aR)-3-[(3S)-3-hydroxypentyl]-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol;
CAS Number	58434-44-9;
PubChem CID	101594562;
ChemSpider	23130105;
Chemical and physical data
Formula	C21H30O3
Molar mass	330.468 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H](O)CCc1cc2OC(C)(C)[C@@H]3CCC(C)=C[C@H]3c2c(O)c1;
	InChI 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 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]

References

^ 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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[pmid1493-1] 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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Identifiers

IUPAC name (6aR,10aR)-3-[(3S)-3-hydroxypentyl]-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number	58434-44-9
PubChem CID	101594562
ChemSpider	23130105
Chemical and physical data
Formula	C₂₁H₃₀O₃
Molar mass	330.468 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC[C@H](O)CCc1cc2OC(C)(C)[C@@H]3CCC(C)=C[C@H]3c2c(O)c1
InChI 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

See also

References