Pyrrole esters of tropanols and related structures as analgesics.
2,4,5-Trimethylpyrrole-3-carboxylic acid esters of tropanols and related monocyclic amino alcohols were synthesized and evaluated for analgesic activity by the mouse hot-plate and Nilsen methods. 1-Methyl-4-piperidinol 4-(2,4,5-trimethylpyrrole-3-carboxylate) (7) exhibited activity in the morphine--codeine range (mouse hot plate). In monkeys, 7 acted neither as a typical narcotic agonist nor as a typical antagonist and it showed no physical dependence liability of the morphine-type. Whereas the pethidine and prodine analgesics have quaternary phenyl substituion at C-4 of the piperidine ring, compound 7 does not.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D000882:Haplorhini; D051379:Mice; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship; D014326:Tropanes / Q000138:chemical synthesis* / Q000494:pharmacology
D000700:Analgesics; D011758:Pyrroles; D014326:Tropanes