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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]
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 .
Cannabinoids (/ k ə ˈ n æ b ə n ɔɪ d z ˌ ˈ k æ n ə b ə n ɔɪ d z /) are compounds found in the cannabis plant or synthetic compounds that can interact with the endocannabinoid system. [1] [2] The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating compound in cannabis.
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.
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).
Hexahydrocannabutol (HHCB, HHC-B) is a semi-synthetic cannabinoid derivative, the hydrogenated derivative of tetrahydrocannabutol (THCB). It was first synthesised by Roger Adams in 1942 and produces only weak cannabinoid-like effects in animals. [1]
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.
HHCP-O-acetate (HHCPO, HHCP-O) is a semi-synthetic derivative of tetrahydrocannabiphorol (THCP) derived in several steps by hydrogenation to hexahydrocannabiphorol (HHCP) followed by acetylation of the OH group.