Phenolic analogues of reversed esters of pethidine

Abstract

The preparation and stereochemical characterization of phenolic analogues of the reversed ester of pethidine, alpha- and beta-prodine and a 1-phenethyl congener are described. All the compounds were weakly active or inactive as agonists in rodent antinociceptive tests and failed to antagonize fentanyl in rats. The results substantiate the view that the morphine and 4-phenylpiperidine groups of analgesics differ in their modes of interaction with opiate receptors, except possibly when the piperidine derivative carries a C-4 carbon substituent.