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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
Author(s) -
Hallström Gösta,
Lindeke Björn
Publication year - 1981
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200081010
Subject(s) - succinimide , chemistry , mass spectrometry , deuterium , decomposition , oxide , gas chromatography , chromatography , gas chromatography–mass spectrometry , organic chemistry , physics , quantum mechanics
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.