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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]
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. [2] [3]
Delta-9-THC was discovered to partly metabolize into 11-Hydroxy-THC and alpha,10 alpha-epoxy-hexahydrocannabinol along with 1,2-epoxy-hexahydrocannabinol. [17] Cannabidiol was discovered to partly metabolize into 9α-hydroxy-HHC and 8-hydroxy-iso-HHC inside the body. In the presence of alcohol, the methoxy or ethoxy analogs such as 9-methoxy ...
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.
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.
AM-906 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist.It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between CB 1 and CB 2 receptors. [1]
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.