The biotransformation of methadone in man: Synthesis and identification of a major metabolite

Abstract

After administration of methadone to man, only two basic urinary excretion products were detected, these were unchanged drug and 2-ethyl-1, 5-dimethyl-3, 3-diphenyl-1-pyrroline. The hydriodide of the latter was synthesized and its endocyclic alkene structure was confirmed from infrared and nuclear magnetic resonance spectral data. This compound was shown to be identical with the hydriodide of the basic product formed by reaction of 1, 5-dimethyl-3, 3-diphenylpyrrolid-2-one with ethyl-lithium.