11-Hydroxy-Δ8-THC

{{Short description|Metabolite of delta-8-THC}}

{{DISPLAYTITLE:11-Hydroxy-Δ⁸-THC}}

{{For|the isomer of this chemical inherited from Δ⁹-tetrahydrocannabinol|11-Hydroxy-THC}}

{{Primary sources|date=January 2023}}

{{cs1 config|name-list-style=vanc}}

{{Infobox drug

| drug_name = 11-Hydroxy-Δ⁸-THC

| IUPAC_name = (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol

| image = 11-OH-D8-THC_structure.png

| image_class = skin-invert-image

| width = 220

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number = 28646-40-4

| CAS_number_Ref = {{Cascite|changed|EPA}}

| ATC_prefix = None

| PubChem = 185651

| ChemSpiderID = 161395

| ChEMBL =

| synonyms = 7-OH-Δ⁶-THC

| ChEBI =

| UNII = GM4TR07BPX

| C = 21

| H = 30

| O = 3

| smiles = CCCCCC1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)CO)O

| StdInChI = 1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h8,11-12,16-17,22-23H,4-7,9-10,13H2,1-3H3/t16-,17-/m1/s1

| StdInChIKey = LOUSQMWLMDHRIK-IAGOWNOFSA-N

| class = Cannabinoid

}}

11-Hydroxy-Δ⁸-tetrahydrocannabinol (11-hydroxy-Δ⁸-THC, alternatively numbered as 7-hydroxy-Δ⁶-THC) is an active metabolite of Δ⁸-THC, a psychoactive cannabinoid found in small amounts in Cannabis. It is an isomer of 11-OH-Δ⁹-THC, and is produced via the same metabolic pathway. It was the first cannabinoid metabolite discovered in 1970.{{cite journal | vauthors = Mechoulam R, Hanus L | title = A historical overview of chemical research on cannabinoids | journal = Chemistry and Physics of Lipids | volume = 108 | issue = 1–2 | pages = 1–13 | date = November 2000 | pmid = 11106779 | doi = 10.1016/s0009-3084(00)00184-5 }}

It retains psychoactive effects in animal studies with higher potency than Δ⁸-THC but lower potency than 11-OH-Δ⁹-THC. With widespread legal use of semi-synthetic Δ⁸-THC in certain jurisdictions where Δ⁹-THC remains illegal, 11-OH-Δ⁸-THC is now an important metabolite for distinguishing between use of hemp-derived Δ⁸-THC and natural Δ⁹-THC.{{cite journal | vauthors = Watanabe K, Yamamoto I, Oguri K, Yoshimura H | title = Identification and determination of 11-oxo-delta8-tetrahydrocannabinol as an intermediate metabolite of delta8-tetrahydrocannabinol in the mouse brain and liver | journal = Journal of Pharmacobio-Dynamics | volume = 3 | issue = 12 | pages = 686–91 | date = December 1980 | pmid = 6268770 | doi = 10.1248/bpb1978.3.686 | doi-access = free }}{{cite journal | vauthors = Watanabe K, Yamamoto I, Oguri K, Yoshimura H | title = Metabolic disposition of delta 8-tetrahydrocannabinol and its active metabolites, 11-hydroxy-delta 8-tetrahydrocannabinol and 11-oxo-delta 8-tetrahydrocannabinol, in mice | journal = Drug Metabolism and Disposition | year = 1981 | volume = 9 | issue = 3 | pages = 261–4 | pmid = 6113937 }}{{cite book | vauthors = Järbe TU, Mathis DA | chapter = Discriminative stimulus functions of cannabinoids/cannabimimetics | title = Drug Discrimination: Applications to Drug Abuse Research | series = NIDA Research Monograph | volume = | issue = 116 | pages = 75–99 | date = 1991 | pmid = 1369683 | doi = | url = }}{{cite journal | vauthors = Yamamoto I, Kimura T, Kamei A, Yoshida H, Watanabe K, Ho IK, Yoshimura H | title = Competitive inhibition of delta8-tetrahydrocannabinol and its active metabolites for cannabinoid receptor binding | journal = Biological & Pharmaceutical Bulletin | volume = 21 | issue = 4 | pages = 408–10 | date = April 1998 | pmid = 9586583 | doi = 10.1248/bpb.21.408 | doi-access = free }}{{cite journal | vauthors = Chan-Hosokawa A, Nguyen L, Lattanzio N, Adams WR | title = Emergence of Delta-8 Tetrahydrocannabinol (THC) in DUID Investigation Casework: Method Development, Validation and Application | journal = Journal of Analytical Toxicology | volume = 46| issue = 1| date = March 2021 | pages = 1–9 | pmid = 33754645 | doi = 10.1093/jat/bkab029 | doi-access = free }}