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Identification of a nitrone as an in vitro metabolite of N ‐methylamphetamine
Author(s) -
Coutts R. T.,
Jones G. R.,
Liu S.F.
Publication year - 1978
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.1200050609
Subject(s) - nitrone , methylamine , metabolite , chemistry , in vitro , chromatography , gas chromatography , adduct , formaldehyde , biochemistry , organic chemistry , cycloaddition , catalysis
The relatively labile nitrone, α‐methyl‐( N ‐methylene)benzeneethanamine N ‐oxide was isolated from incubates of (±)‐ N ‐methylamphetamine with fortified liver homogenates from rats and rabbit. Identification of the nitrone was confirmed directly by gas chromatography and gas chromatography mass spectrometry and, after its conversion to isoxazolidine adducts by the action of methyl and ethyl acrylate. An authentic sample of the nitrone was synthesized unequivocally from N ‐hydroxyamphetamine and formaldehyde. The isomeric nitrone, N ‐(α‐methylbenzeneethylidene)methylamine N ‐oxide, was also synthesized and its gas chromatographic and gas chromatographic mass spectrometric characteristics determined to confirm that the metabolically formed nitrone was not N ‐(α‐methylbenzeneethylidene)methylamine N ‐oxide. Two previously unreported metabolites of (±)‐ N ‐methylamphetamine, N ‐hydroxyamphetamine and 1‐hydroxy‐1‐phenyl‐2‐propanone, were isolated from rat in vitro experiments; the latter metabolite was not produced in vitro by rabbit liver homogenates.