The identification, properties and analysis of N-hydroxyamphetamine—a metabolite of amphetamine

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Abstract
N-Hydroxyamphetamine (Ib) can be extracted from aqueous solutions at neutral pH, but is readily decomposed into syn- and anti-phenylacetone oximes (II) at alkaline pH values. Gas chromatography of Ib is possible, provided the compound does not come into contact with heated metal surfaces. In aqueous media the hydroxylamine can be determined (1) by extraction from the medium with ether and analysis of the ethereal solution by g.l.c.; (2) by separation of the compound on a thin-layer then oxidation of the hydroxylamine spot with ammoniacal silver nitrate to give phenylacetone oximes which may then be determined by g.l.c.; (3) by reduction with lithium aluminium hydride to amphetamine (Ia) followed by g.l.c.; (4) conversion to phenylacetone oximes by shaking at pH 12 in air, extraction of the oximes, followed by g.l.c.; (5) Alternatively, N-hydroxyamphetamine can be determined directly in aqueous solution by polarography provided the measurement is made immediately after the supporting electrolyte, sulphite/NaOH, has been added.