53989-32-5Relevant academic research and scientific papers
Cannabinol derivatives: Binding to cannabinoid receptors and inhibition of adenylylcyclase
Rhee, Man-Hee,Vogel, Zvi,Barg, Jacob,Bayewitch, Michael,Levy, Rivka,Hanu?, Lumir,Breuer, Aviva,Mechoulam, Raphael
, p. 3228 - 3233 (1997)
Several derivatives of cannabinol and the 1,1-dimethylheptyl homolog (DMH) of cannabinol were prepared and assayed for binding to the brain and the peripheral cannabinoid receptors (CB1 and CB2), as well as for activation of CB1- and CB2-mediated inhibition of adenylylcyclase. The DMH derivatives were much more potent than the pentyl (i.e., cannabinol) derivatives. 11-Hydroxycannabinol (4a) was found to bind potently to both CB1 and CB2 (K(i) values of 38.0 ± 7.2 and 26.6 ± 5.5 nM, respectively) and to inhibit CB1-mediated adenylylcyclase with an EC50 of 58.1 ± 6.2 nM but to cause only 20% inhibition of CB2-mediated adenylylcyclase at 10 μM. It behaves as a specific, though not potent, CB2 antagonist. 11- Hydroxycannabinol-DMH (4b) is a very potent agonist for both CB1 and CB2 (K(i) values of 100 ± 50 and 200 ± 40 pM; EC50 of adenylylcyclase inhibition 56.2 ± 4.2 and 207.5 ± 27.8 pM, respectively).
Cannabis. Part 27. Synthesis of 8-, 10-, and 11-Oxygenated Cannabinols
Novak, Jiri,Salemink, Cornelis A.
, p. 2867 - 2871 (2007/10/02)
Two metabolites of cannabinol (1-hydroxy-6,6,9-trimethyl-3-pentyl-6H-dibenzopyran) in man, 11-hydroxycannabinol (8) and 1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid (7), have been totally synthesized together with three possible metabolites, 11-oxocannabinol (9), 8-hydroxycannabinol (15), and 10-hydroxycannabinol (21).This is the first total synthesis of the novel compound (21) and the previously isolated acid (7) and occurs in high yield; compounds (8), (9), and (15) were obtained in substantially higher yields than had been achieved by partial synthesis only.The key step in these syntheses was the regiospecific formation of the aryl-aryl bond via nucleophilic aromatic substitution of the methoxy group in the o-methoxyaryldihydro-oxazoles (2), (11), and (17) by the Grignard reagent, 2,6-dimethoxy-4-pentylphenylmagnesium bromide.The acid (7) was prepared from the new and possibly psychoactive 9-bromo-9-norcannabinol (6), which was obtained from 4-bromo-2-methoxybenzoic acid.Reduction of the acid (7) with lithium aluminium hydride gave 11-hydroxycannabinol, which was oxidized by Jones reagent to 11-oxocannabinol. 8- and 11-Hydroxycannabinol were synthesized in several steps from 2,5-dimethoxy-p-toluic acid and 2,3-dimethoxy-p-toluic acid, respectively.
