On the chemical stability of beta-hydroxyphenylalkylhydroxylamines and its relevance to the metabolism of amphetamines and ephedrines. |
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Authors: | B Lindeke A K Cho U Jonsson U Paulsen |
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Institution: | Department of Organic Pharmaceutical Chemistry Biomedical Center University of Uppsala, Box 574 S-751 23 Uppsala, Sweden |
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Abstract: | β, N-bis (hydroxy) phenylalkylamines rapid oxidative decomposition to benzaldehyde and an oxime in the presence of small quantities of Cu(II). The reaction occurs in aqueous solution at pH 7.4 so that products of metabolic transformation reactions involving the oxidation of such hydroxylamines would be expected to decompose in this way. N-Oxidation of norephedrine would result in benzaldehyde by this mechanism, and since benzaldehyde is a precursor to benzoic acid, it is proposed that the N-hydroxylation pathway of arylalkylamine metabolism instead of carbon oxidation could lead to benzoic acid. This acid is a major metabolite of compounds such as amphetamine and ephedrine in some species. |
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