3'-Hydroxy-THC

{{Short description|Minor metabolite of THC}}

{{Drugbox

| IUPAC_name = (6aR,10aR)-3-[(3S)-3-hydroxypentyl]-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol

| image = 3'-OH-THC_structure.png

| image_class = skin-invert-image

| width = 220

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number = 93246-26-5

| PubChem = 101594562

| ChemSpiderID = 23130105

| ChEMBL =

| ChEBI =

| UNII =

| C=21 | H=30 | O=3

| smiles = CC[C@H](O)CCc1cc2OC(C)(C)[C@@H]3CCC(C)=C[C@H]3c2c(O)c1

| StdInChI=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

| StdInChIKey = 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.{{cite journal | vauthors = Widman M, Nordqvist M, Dollery CT, Briant RH | title = Metabolism of delta1-tetrahydrocannabinol by the isolated perfused dog lung. Comparison with in vitro liver metabolism | journal = The Journal of Pharmacy and Pharmacology | volume = 27 | issue = 11 | pages = 842–8 | date = November 1975 | pmid = 1493 | doi = 10.1111/j.2042-7158.1975.tb10227.x | s2cid = 25711286 }}{{cite book | vauthors = Agurell S, Binder M, Fonseka K, Lindgren JE, Leander K, Martin B, Nilsson IM, Nordqvist M, Ohlsson A, Widman M | display-authors = 6 | chapter = Cannabinoids: Metabolites hydroxylated in the pentyl side chain. | veditors = Nahas GG, Paton WD, Idänpään-Heikkilä JE | title = Marihuana | date = 1976 | pages = 141–157 | publisher = Springer | location = Berlin, Heidelberg | doi = 10.1007/978-3-642-51624-5_12 | isbn = 978-3-642-51626-9 }}{{cite journal | vauthors = Handrick GR, Duffley RP, Lambert G, Murphy JG, Dalzell HC, Howes JF, Razdan RK, Martin BR, Harris LS, Dewey WL | display-authors = 6 | title = 3'-Hydroxy- and (+/-)-3',11-dihydroxy-delta 9-tetrahydrocannabinol: biologically active metabolites of delta 9-tetrahydrocannabinol | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 12 | pages = 1447–50 | date = December 1982 | pmid = 6296389 | doi = 10.1021/jm00354a011 }}{{cite journal | vauthors = Martin BR, Kallman MJ, Kaempf GF, Harris LS, Dewey WL, Razdan RK | title = Pharmacological potency of R- and S-3'-hydroxy-delta 9-tetrahydrocannabinol: additional structural requirement for cannabinoid activity | journal = Pharmacology, Biochemistry, and Behavior | volume = 21 | issue = 1 | pages = 61–5 | date = July 1984 | pmid = 6087379 | doi = 10.1016/0091-3057(84)90131-x | s2cid = 45091289 }}{{cite journal | vauthors = Huestis MA | title = Human cannabinoid pharmacokinetics | journal = Chemistry & Biodiversity | volume = 4 | issue = 8 | pages = 1770–804 | date = August 2007 | pmid = 17712819 | doi = 10.1002/cbdv.200790152 | pmc = 2689518 }}