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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. [2]
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]
The same study found Delta-9-THC to have a binding affinity of 15nM ± 4.4nM at CB1 and 9.1nM ± 3.6nM at CB2. 9R-HHC has a lower selectivity for CB2 (1.2x) compared to D9-THC (1.6x). 9R -HHC has an EC50 of 3.4nM ± 1.5nM at CB1 and 6.2nM ± 2.1nM at CB2 while 9S -HHC has an EC50 of 57nM ± 19nM at CB1 and 55nM ± 10nM at CB2.
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 ...
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.