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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.
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]
Hexahydrocannabiphorol (HHCP, sometimes mistakenly referred to as hexahydroxycannabiphorol) is a semi-synthetic cannabinoid derivative which has been marketed since around 2021. [1] [2] It is believed to be made from the hydrogenation of tetrahydrocannabiphorol (THCP). THCP is only reported as a trace component of cannabis in 2019. [3]
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.
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.
HHC-acetate (Hexahydrocannabinol-O-acetate, HHC-O) is a semi-synthetic cannabinoid derivative which has been marketed since around 2022. [ 1 ] [ 2 ] It is believed to be made in a three step process from cannabidiol extracted from hemp . [ 3 ]
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.
Cannabinoids and their K i values [a] Name Class K i / nM at CB 1 K i / nM at CB 2 Selectivity Structure JWH-004: Naphthoylindole: 48 ± 13: 4 ± 1.5: CB 2 (12x) JWH-007 [5] Naphthoylindole: 9.5 ± 4.5: 2.9 ± 2.6: CB 2 (3.3x) JWH-009: Naphthoylindole >10000: 141 ± 14: CB 2 (>70x) JWH-011: Naphthoylindole: JWH-015 [5] Naphthoylindole: 164 ± ...