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Four stereoisomers of 8-OH-HHC arise from C8-hydroxylation of hexahydrocannabinol. There are four possible 8-OH-HHC metabolites arising from naturally derived HHCs: cis-and trans-8-OH-9α-HHC & cis-and trans-8-OH-9β-HHC. All four have been prepared synthetically to probe stereochemical effects on cannabinoid biological activity. [5]
9-Hydroxyhexahydrocannabinol (9-OH-HHC) is a semi-synthetic derivative of tetrahydrocannabinol. It is formed as an impurity in the synthesis of Delta-8-THC, [1] and retains activity in animal studies though with only around 1/10 the potency of Δ 9-THC, with the 9α- and 9β- enantiomers having around the same potency. [2]
9-Nor-9β-hydroxyhexahydrocannabinol (9-nor-9beta-HHC; sometimes incorrectly confused with 11-nor-9β-hydroxyhexahydrocannabinol [1]) is a cannabinoid first discovered from early modifications to the structure of THC, in a search for the simplest compound that could still fulfill the binding requirements to produce cannabis-like activity. [2] [3]
HHC-P is a partial agonist of the CB1 receptors with an EC50 of 44.4nM for 9R-HHCP and 134nM for 9S-HHCP. Compared to Hexahydrocannabinol (HHC) with an EC50 of 101nM for 9R-HHC and 1,190nM for 9S-HHC [ 5 ] In 2021, HHC-P was positively identified in multiple retail electronic vaping products in the United States.
The 11-OH-9β-HHC isomer is the structurally related methylene homologue of 11-Nor-9β-hydroxyhexahydrocannabinol also known as 9-Nor-9β-hydroxyhexahydrocannabinol. [8] [9] 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.
Δ-8-tetrahydrocannabinol (delta-8-THC, [a] Δ 8-THC) is a psychoactive cannabinoid found in the cannabis plant. [1] It is an isomer of delta-9-tetrahydrocannabinol (delta-9-THC, Δ 9-THC), the compound commonly known as THC, with which it co-occurs in hemp; natural quantities of ∆ 8-THC found in hemp are low.
Hexahydrocannabivarin (HHCV, HHC-V) is a semi-synthetic cannabinoid derivative, the hydrogenated derivative of tetrahydrocannabivarin (THCV). It was first synthesised by Roger Adams in 1942 and produces only weak cannabinoid-like effects in animals. [ 1 ]
Like Δ 9-THC, 11-hydroxy-THC is a partial agonist at the cannabinoid receptor CB 1, but with significantly higher binding affinity (K i = 0.37 nM compared to Δ 9-THC K i = 35 nM). [7] With respect to cAMP inhibition at CB 1 it displays a similar efficacy to that of Δ 9 -THC (EC 50 = 11 nM vs. EC 50 = 5.2 nM, respectively), but a lower ...