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A re‐examination of the synthesis and some properties of the in vitro metabolite, N ‐hydroxyphenmetrazine
Author(s) -
Coutts R. T.,
Dawe R.,
Beckett A. H.
Publication year - 1975
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.1200020307
Subject(s) - mass spectrometry , yield (engineering) , metabolite , chemistry , chromatography , derivative (finance) , thin layer chromatography , gas chromatography , in vitro , biochemistry , materials science , economics , financial economics , metallurgy
The reported synthesis of N ‐hydroxyphenmetrazine from phenmetrazine by the action of m ‐chloroperbenzoic acid could not be repeated. When the synthetic procedure was modified N ‐hydroxyphenmetrazine was obtained in low yield. The product had different properties from those claimed previously, but was identical to metabolically produced N ‐hydroxyphenmetrazine. It was characterized by means of thin‐layer chromatography, combined gas chromatography and mass spectrometry, preparation of a t ‐butyldimethylsilyl derivative and oxidation to a mixture of nitrones. Mass spectrometry was also used to characterize these derivatives.