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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 ...
Like Δ 9-THC, 11-hydroxy-THC is a partial agonist at the cannabinoid receptor CB 1, but with significantly higher binding affinity (K i = 0.37 nM compared to Δ 9-THC K i = 35 nM). [7] With respect to cAMP inhibition at CB 1 it displays a similar efficacy to that of Δ 9 -THC (EC 50 = 11 nM vs. EC 50 = 5.2 nM, respectively), but a lower ...
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.
The EC50 shows 9R-HHC has a lower selectivity for CB2 (0.55x) compared to THC (1.5x). HHC has been typically described as weaker than Delta-9-THC in psychoactive effects. HHC produces 11-Hydroxyhexahydrocannabinol and 8-Hydroxyhexahydrocannabinol among others as a metabolite which may contribute to its overall effect. [6] [7]
11-Hydroxy-Δ-8-tetrahydrocannabinol (11-OH-Δ 8-THC, alternatively numbered as 7-OH-Δ 6-THC) is an active metabolite of Δ 8-THC, a psychoactive cannabinoid found in small amounts in cannabis. It is an isomer of 11-OH-Δ 9-THC, and is produced via the same metabolic pathway. It was the first cannabinoid metabolite discovered in 1970. [1]
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]
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.
11-Hydroxycannabinol (11-OH-CBN) is the main active metabolite of cannabinol (CBN), one of the active components of cannabis, [1] and has also been isolated from cannabis itself. [2] It is more potent than CBN itself, acting as an agonist of CB 1 with around the same potency as THC, but is a weak antagonist at CB 2. [3] [4]