Agonist-antagonist actions and stereoselectivity of optical pairs of some N-substituted alpha-N-normetazocines.
alpha-(-)-, (+)-, and (+/-)-N-4-Methylpentyl-, (-)- and (+)-N-cis-3-chloroallyl-, and (-)- and (+)-N-propynyl-N-normetazocine (I, II, and III, respectively) have been prepared from alpha-(-)-, (+)-, 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 scrutiny in animal and human studies.
D000700:Analgesics / Q000494:pharmacology*; D000818:Animals; D016227:Benzoquinones; D055598:Chemical Phenomena; D002621:Chemistry; D003496:Cyclazocine / Q000031:analogs & derivatives* / Q000494:pharmacology; D005260:Female; D006801:Humans; D008253:Macaca mulatta; D008297:Male; D051379:Mice; D009021:Morphine Dependence / Q000503:physiopathology; D009292:Narcotic Antagonists; D010146:Pain / Q000139:chemically induced; D011809:Quinones; D011930:Reaction Time / Q000187:drug effects; D013237:Stereoisomerism
D000700:Analgesics; D016227:Benzoquinones; D009292:Narcotic Antagonists; D011809:Quinones; C014716:normetazocine; C029322:phenylbenzoquinone; D003496:Cyclazocine