Agonist-antagonist actions and stereoselectivity of optical pairs of some N-substituted α-N-normetazocines

Article abstract of DOI:10.1002/jps.2600731260

α-(-)-, (+)-, and (±)-N-4-Methylphenyl-, (-)- and (+)-N-cis-3-chloroallyl-, and (-) and (+)-N-propynyl-N-normetazocine (I, II, and III, respectively) have been prepared from α-(-)-, (+)-, and (±)-N-normetazocine (IV) and tested for antinociceptive activity in mice and in morphine-dependent rhesus monkeys. The results obtained with Ia and b somewhat resemble the results obtained with the corresponding phenazocine isomers, whereas those observed with IIa and b more nearly correspond with those reported for (+)- and (-)-N-allyl-N-normetazocine (SKF 10,047; NANM). The propynyl isomers (IIIa and b) display profiles of activity more closely like the corresponding isomers of metazocine. Evidence is considered which suggests that some of the (+)-isomers merit closer scrunity in animal and human studies.