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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.
They have drawn research interest for their role in HHC toxicology and stereoisomeric probes of the cannabinoid drug/receptor interaction. 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 ]
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.
Like other 11-OH cannabinoid metabolites, 11-OH-9β-HHC retains activity comparable to HHC itself while the 9α-isomer is significantly less active. [5] However, upon formation it is rapidly metabolized further to the inactive 11-carboxylates, producing a shortened half-life within the body and lowering its bioavailability considerably through ...
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.
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.
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]
CBN was the first cannabinoid to be isolated from cannabis extract in the late 1800s. Specifically, it was discovered by Barlow Wood, Newton Spivey, and Easterfield in 1896. [ 21 ] In the early 1930s, CBN's structure was identified by Cahn , [ 22 ] [ 23 ] marking the first development of a cannabis extract .