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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.
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.
9-Nor-9β-hydroxyhexahydrocannabinol (9-nor-9beta-HHC; sometimes incorrectly confused with 11-nor-9β-hydroxyhexahydrocannabinol [1]) is a cannabinoid first discovered from early modifications to the structure of THC, in a search for the simplest compound that could still fulfill the binding requirements to produce cannabis-like activity.
These are achieved at lower doses, because many synthetic cannabinoids are more potent than marijuana, and users are often unaware of exactly what they are getting and how potent it is. [55] For example, Δ 9-THC has an EC 50 of 250 nM at CB 1 and 1157 nM at CB 2, whereas PB-22 has an EC 50 of 5.1 nM at CB 1 and 37 nM at CB 2. [8]
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.
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.
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.