title: Racemic and optically active 1,3,3-trimethyl-4-phenyl-4-(propionyloxy)piperidine.
abstract: The preparation and resolution of 1,3,3-trimethyl-4-phenyl-4-(propionyloxy)piperidine (5,3-methylprodine) are described, and the results of the antinociceptive activities of the products by hot-plate (mice) and tail-withdrawal (rats) tests are shown to support proposals made from a recent analysis of the stereochemical structure-activity relationships of C-methyl derivatives of the reversed ester of meperidine. Data of absolute configuration were obtained by X-ray crystallography of a hydrobromide salt.
mesh_terms: D000522:Alphaprodine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000698:Analgesia; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D051379:Mice; D008968:Molecular Conformation; D051381:Rats; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: D000522:Alphaprodine; C047292:1,3,3-trimethyl-4-phenyl-4-(propionyloxy)piperidine