Metabolic N ‐oxidation of α‐acetylenic amines—A gas chromatographic mass spectrometric investigation of the chemical decomposition of N ‐(5‐pyrrolidinopent‐3‐ynyl)succinimide N' ‐oxide using deuterium substitution

On gas chromatographic analysis, N ‐(5‐pyrrolidinopent‐3‐ynyl)succinimide N '‐oxide gave rise to three main decomposition products, which were assigned the structures N ‐(3‐oxopent‐4‐enyl)succinimide, N ‐(penta‐3, 4‐dienyl)succinimide and N ‐(3‐pyrrolidino‐3‐oxopropyl)succinimide. These three products were identified by electron impact mass spectrometry, using deuterium substituted N ‐oxides, and mechanisms for the formation of the former two are proposed. By gas chromatographic mass spectrometric analysis, extracts from metabolic incubations of N ‐(5‐pyrrolidinopent‐3‐ynyl)succinimide were shown to contain the N ‐oxide, as previously indicated by indirect methods.