Synthesis and pharmacology of a hybrid cannabinoid Original Research Article

A pentacyclic hybrid cannabinoid () has been synthesized, which combines structural elements of traditional cannabinoids and cannabmimetic indoles. Cannabinoid contains a 1-pentylindole structure fused to the 2,3-positions of the partially reduced hydroxydibenzopyran system of THC. The successful approach to employed 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole () as the starting material. Dehydrogenation to carbazole , followed by demethylation and condensation with trans-p-menthadienol gave N-benzoyl hybrid cannabinoid , N-alkylation of which afforded target cannabinoid . The hybrid cannabinoid had affinity for the CB1 receptor approximately equal to that of Δ8-THC (Ki=19.3±3 nM), and shows comparable potency in vivo.