Synthesis and narcotic agonist-antagonist evaluation of some 2,6-methano-3-benzazocine-11-propanols. Analogs of the ring C bridged oripavine-7-methanols

Abstract

A general synthesis of variously substituted 2,6-methano-3-benzazocine-11-propanols is described. Nine N-CH3 derivatives and their corresponding N-cyclopropylmethyl counterparts were prepared and studied in the mouse acetylcholine induced writhing and rat phenazocine antagonism tests. The results are compared with literature information on the bridged oripavine methanols. It is concluded that the synthetic analogues have a different structure-activity profile, in general being weak agonists but potent antagonists.