Synthesis and Analgesic Activity of Cyclohexenylmethylamines and Related Compounds

Abstract

N, N-Dimethyl-(6-benzyl-2-cyclohexenyl) methylamine derivatives (I) were prepared by dehydrochlorination of the 1, 2-cis-N, N-dimethyl-(6-benzyl-2-chlorocyclohexyl) methylamines (XII), which were obtained by the reaction of the 1, 2-trans-cyclohexanol derivatives (X) with thionyl chloride. The cyclohexenylmethylamine derivatives and related compounds were examined for analgesic activity by using the phenylquinone writhing method. Some of them, in particular, 1, 6-trans-N, N-dimethyl-(6-benzyl-4, 4-dimethyl-2-cyclohexenyl) methylamine hydrochloride (37) showed pronounced pharmacological activities. Structure-activity relationships are discussed.