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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]
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.
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] More recently it has been sold as an ingredient in grey-market cannabinoid products. [2]
CP-47,497-C8 is made by extending the dimethylheptyl side chain of CP-47,497 to a dimethyloctyl side chain. It was discovered by forensic scientists in a herbal blend known as "Spice" in 2008, along with JWH-018, an aminoalkylindole. [8] Hybrid cannabinoids have a combination of classical and non-classical cannabinoid structural features. [84]
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. [1] [2] HHCH was first identified as a designer drug in Sweden in September 2023. [3]
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 ]
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] More recently it has been sold as an ingredient in grey-market cannabinoid products.