11-Hydroxyhexahydrocannabinol

Chemical compound vanc 6 (6aR,9R,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol 11-OH-HHC Alpha and Beta.png skin-invert-image 220 64663-39-4 127684 113271 21 32 3 CCCCCC1=CC(=C2[C@@H]3C[C@@H](CC[C@H]3C(OC2=C1)(C)C)CO)O 1S/C21H32O3/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/h11-12,15-17,22-23H,4-10,13H2,1-3H3/t15-,16-,17-/m1/s1 LXSFNMQURHTPIT-BRWVUGGUSA-N 11-Hydroxyhexahydrocannabinol (11-OH-9α-HHC and 11-OH-9β-HHC, or alternatively 7-OH-HHC under the monoterpenoid numbering system) is an active metabolite of tetrahydrocannabinol (THC) and a metabolite of the trace cannabinoid hexahydrocannabinol (HHC). Järbe TU, Hiltunen AJ, Lander N, Mechoulam R Cannabimimetic activity (delta 1-THC cue) of cannabidiol monomethyl ether and two stereoisomeric hexahydrocannabinols in rats and pigeons Pharmacology, Biochemistry, and Behavior 25 2 393–399 August 1986 3020594 10.1016/0091-3057(86)90015-8 28373651 Harvey DJ, Martin BR, Paton WD Comparative in vivo Metabolism of Δ1-tetrahydrocannabinol (Δ1-THC), cannabidiol (CBD) and cannabinol (CBN) by Several Species 1978 Recent Developments in Mass Spectrometry in Biochemistry and Medicine 161–184 Frigerio A Boston, MA Springer US en 10.1007/978-1-4613-3991-5_13 978-1-4613-3993-9 Falck Jørgensen C, Schou Rasmussen B, Linnet K, Thomsen R Evidence of 11-Hydroxy-hexahydrocannabinol and 11-Nor-9-carboxy-hexahydrocannabinol as Novel Human Metabolites of Δ9-Tetrahydrocannabinol Metabolites 13 12 1169 November 2023 38132851 10744638 10.3390/metabo13121169 free In a pathway that parallels the metabolism of the THC family of cannabinoids, following ingestion HHC undergoes hepatic metabolism by cytochrome p450 (predominantly the CYP3A4 isozyme, with some contribution from CYP2C9 and CYP2C19) to a multitude of oxygenated derivatives, including 8-OH-HHC and 11-OH-HHC. C11-oxidation is the major pathway of THC and HHC metabolism. Dinis-Oliveira RJ Metabolomics of Δ9-tetrahydrocannabinol: implications in toxicity Drug Metabolism Reviews 48 1 80–87 2016-01-02 26828228 10.3109/03602532.2015.1137307 32913023 class=skin-invert-image|frameless|650x650px Like other 11-OH cannabinoid metabolites, 11-OH-9β-HHC retains activity comparable to HHC itself while the 9α-isomer is significantly less active. Mechoulam R, Lander N, Varkony TH, Kimmel I, Becker O, Ben-Zvi Z, Edery H, Porath G Stereochemical requirements for cannabinoid activity Journal of Medicinal Chemistry 23 10 1068–1072 October 1980 7420350 10.1021/jm00184a002 However, upon formation it is rapidly metabolized further to the inactive 11-carboxylates, producing a shortened half-life within the body and lowering its bioavailability considerably through first-pass metabolism. Huestis MA Human cannabinoid pharmacokinetics Chemistry & Biodiversity 4 8 1770–1804 August 2007 17712819 2689518 10.1002/cbdv.200790152 Lewis J, Molnar A, Allsop D, Copeland J, Fu S Rapid elimination of Carboxy-THC in a cohort of chronic cannabis users International Journal of Legal Medicine 130 1 147–152 January 2016 26233612 10.1007/s00414-015-1241-z 25318521 The 11-OH-9β-HHC isomer is the structurally related methylene homologue of 11-Nor-9β-hydroxyhexahydrocannabinol also known as 9-Nor-9β-hydroxyhexahydrocannabinol. https://pubchem.ncbi.nlm.nih.gov/compound/6452587#section=Structures 9-Hydroxy-9-norhexahydrocannabinol PubChem U.S. National Library of Medicine https://pubchem.ncbi.nlm.nih.gov/compound/127684#section=Structures 7-Hydroxyhexahydrocannabinol PubChem U.S. National Library of Medicine HU-243 is a synthetic analog of 11-OH-9β-HHC in which the natural n-pentyl side chain is replaced with a geminal-dimethylheptyl substitution. This significantly increases HU-243s binding affinity for the CB1 and CB2 receptors. Devane WA, Breuer A, Sheskin T, Järbe TU, Eisen MS, Mechoulam R A novel probe for the cannabinoid receptor Journal of Medicinal Chemistry 35 11 2065–2069 May 1992 1317925 10.1021/jm00089a018 See also 9-Hydroxyhexahydrocannabinol 9-Nor-9β-hydroxyhexahydrocannabinol 11-Hydroxycannabinol HU-210 8-hydroxyhexahydrocannabinol References 30em Category:Benzochromenes Category:Cannabinoids Category:Recreational drug metabolites