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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-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 ]
Hexahydrocannabihexol (HHCH) is a semi-synthetic cannabinoid derivative. It was first synthesised by Roger Adams in 1942 and found to be more potent than either the pentyl or heptyl homologues, or the unsaturated tetrahydrocannabinol analogue.
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 Δ9-THC and Δ8-THC, HHC is processed by cytochrome P450 (CYP3A4, CYP2C9 and CYP2C19) to a series of oxygenated derivatives, some of which maintain activity. [1] While 11-OH-HHC and its downstream products are the major metabolites of HHC metabolism, hydroxylation at C8 plays a varyingly significant role in animal species.
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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.
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). [1] [2] [3] In a pathway that parallels the metabolism of the THC family of cannabinoids ...