:11-Hydroxy-THC

{{Short description|Active metabolite of Δ9-THC}}

{{For|the isomer of this chemical inherited from Δ⁸-tetrahydrocannabinol|11-Hydroxy-Delta-8-THC}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477208799

| IUPAC_name = (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol

| image = 11-OH-THC.svg

| image_class = skin-invert-image

| width = 250px

| image2 = 11-Hydroxy-THC-3D-balls.png

| alt2 = 11-Hydroxy-THC molecule

| tradename =

| legal_status =

| legal_UK = Class B

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 36557-05-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9VY04N5SLB

| ATC_prefix = None

| PubChem = 37482

| KEGG = C22778

| synonyms = 11-OH-Δ9-THC; 7-OH-Δ1-THC; 11-hydroxy-THC

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 34385

| class = Cannabinoid

| C = 21

| H = 30

| O = 3

| smiles = Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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/h10-12,16-17,22-23H,4-9,13H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = YCBKSSAWEUDACY-UHFFFAOYSA-N

}}

11-Hydroxy-Δ⁹-tetrahydrocannabinol (11-OH-Δ⁹-THC, alternatively numbered as 7-OH-Δ¹-THC), usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after its consumed.{{cite journal | vauthors = Kraemer T, Paul LD | title = Bioanalytical procedures for determination of drugs of abuse in blood | journal = Analytical and Bioanalytical Chemistry | volume = 388 | issue = 7 | pages = 1415–1435 | date = August 2007 | pmid = 17468860 | doi = 10.1007/s00216-007-1271-6 | s2cid = 32917584 }}{{cite book | vauthors = Huestis MA | title = Cannabinoids | chapter = Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol | series = Handbook of Experimental Pharmacology | volume = 168 | pages = 657–690 | date = 2005 | issue = | pmid = 16596792 | doi = 10.1007/3-540-26573-2_23 | isbn = 3-540-22565-X }}

After cannabis consumption, THC is metabolized inside the body by cytochrome P450 enzymes such as CYP2C9 and CYP3A4 into 11-hydroxy-THC and then further metabolized by dehydrogenase{{which|date=April 2024}} and CYP2C9 enzymes to form 11-nor-9-carboxy-THC (THC-COOH), which is inactive at the CB₁ receptors; and further glucuronidated to form 11-nor-Δ⁹-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ⁹-THC-COOH-glu){{cite journal | vauthors = Stout SM, Cimino NM | title = Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review | journal = Drug Metabolism Reviews | volume = 46 | issue = 1 | pages = 86–95 | date = February 2014 | pmid = 24160757 | doi = 10.3109/03602532.2013.849268 | s2cid = 29133059 | url = https://zenodo.org/record/1093138 }} in the liver, from where it is subsequently excreted through feces and urine (via bile from the liver).{{cite journal | vauthors = Grotenhermen F | title = Pharmacokinetics and pharmacodynamics of cannabinoids | journal = Clinical Pharmacokinetics | volume = 42 | issue = 4 | pages = 327–360 | date = 2003 | pmid = 12648025 | doi = 10.2165/00003088-200342040-00003 | s2cid = 25623600 }} Both metabolites, along with THC, can be assayed in drug tests.

11-hydroxy-THC can be formed after consumption of THC from inhalation (vaping, smoking) and oral (by mouth, edible, sublingual) use, although levels of 11-hydroxy-THC are typically higher when eaten compared to inhalation.{{cite journal | vauthors = Huestis MA, Henningfield JE, Cone EJ | title = Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana | journal = Journal of Analytical Toxicology | volume = 16 | issue = 5 | pages = 276–282 | date = 1992 | pmid = 1338215 | doi = 10.1093/jat/16.5.276 }}{{cite journal | vauthors = Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, Huestis MA | title = Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers | journal = Journal of Analytical Toxicology | volume = 33 | issue = 8 | pages = 469–477 | date = October 2009 | pmid = 19874654 | pmc = 3159863 | doi = 10.1093/jat/33.8.469 }}