11-Hydroxy-THC

Active metabolite of Δ9-THC the isomer of this chemical inherited from Δ8-tetrahydrocannabinol 11-Hydroxy-Δ8-THC11-Hydroxy-Δ8-THC changed changed 477208799 (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 11-OH-THC.svg skin-invert-image 250px 11-Hydroxy-THC-3D-balls.png bg-transparent 11-Hydroxy-THC molecule Class B changed ?? 36557-05-8 correct FDA 9VY04N5SLB None 37482 C22778 11-OH-Δ9-THC; 7-OH-Δ1-THC; 11-hydroxy-THC correct chemspider 34385 Cannabinoid 21 30 3 OC1=C2[C@]3([C@](C(C)(C)OC2=CC(CCCCC)=C1)(CCC(CO)=C3)[H])[H] correct chemspider 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 correct chemspider 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 within cannabis culture, is the main active metabolite of tetrahydrocannabinol (THC), the major psychoactive substance in cannabis. Kraemer T, Paul LD Bioanalytical procedures for determination of drugs of abuse in blood Analytical and Bioanalytical Chemistry 388 7 1415–1435 August 2007 17468860 10.1007/s00216-007-1271-6 32917584 Huestis MA Cannabinoids Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol Handbook of Experimental Pharmacology 168 657–690 2005 16596792 10.1007/3-540-26573-2_23 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 dehydrogenaseApril 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) Stout SM, Cimino NM Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review Drug Metabolism Reviews 46 1 86–95 February 2014 24160757 10.3109/03602532.2013.849268 29133059 https://zenodo.org/record/1093138 in the liver, from where it is subsequently excreted through feces and urine. Grotenhermen F Pharmacokinetics and pharmacodynamics of cannabinoids Clinical Pharmacokinetics 42 4 327–360 2003 12648025 10.2165/00003088-200342040-00003 25623600 Both metabolites can be assayed in drug tests. 11-hydroxy-THC is formed after human consumption of THC containing products regardless of administration route, although levels of 11-hydroxy-THC are typically higher when cannabis products are eaten instead of inhaled. Huestis MA, Henningfield JE, Cone EJ Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana Journal of Analytical Toxicology 16 5 276–282 1992 1338215 10.1093/jat/16.5.276 Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, Huestis MA Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers Journal of Analytical Toxicology 33 8 469–477 October 2009 19874654 3159863 10.1093/jat/33.8.469 Pharmacology Like Δ9-THC, 11-hydroxy-THC is a partial agonist at the cannabinoid receptor CB1, but with significantly higher binding affinity (Ki = 0.37 nM compared to Δ9-THC Ki = 35 nM). Zagzoog A, Cabecinha A, Abramovici H, Laprairie RB Modulation of type 1 cannabinoid receptor activity by cannabinoid by-products from Cannabis sativa and non-cannabis phytomolecules Frontiers in Pharmacology 13 956030 26 August 2022 36091813 10.3389/fphar.2022.956030 9458935 free With respect to cAMP inhibition at CB1 it displays a similar potency to that of Δ9-THC (EC50 = 11 nM vs. EC50 = 5.2 nM, respectively), but a lower maximum response, i.e., efficacy (Emax = 28% vs. Emax = 70%). Research In an in vitro analysis by the University of Rhode Island on cannabinoids it was found that 11-OH-Δ9-THC had the 3rd highest 3C-like protease inhibitor activity against COVID-19 out of all the cannabinoids tested within that study but not as high as the antiviral drug GC376 (56% for 11-OH-Δ9-THC vs. 100% for GC376). Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity Molecules 27 18 6127 September 2022 36144858 9502466 10.3390/molecules27186127 free See also 11-Hydroxy-Delta-8-THC 11-Hydroxyhexahydrocannabinol 3'-Hydroxy-THC 7-Hydroxycannabidiol 10-Hydroxy-THC 8,11-Dihydroxytetrahydrocannabinol 11-Hydroxycannabinol Cannabis edible Delta-11-Tetrahydrocannabinol References Category:Cannabinoids Category:Benzochromenes Category:Primary alcohols Category:Hydroxyarenes Category:Recreational drug metabolites