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Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol (THC). It is a naturally occurring phytocannabinoid that has rarely been identified as a trace component in Cannabis sativa, [1] [2] but can also be produced synthetically by firstly acid cyclization of cannabidiol and then hydrogenation of tetrahydrocannabinol.
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.
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.
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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.
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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]