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Xenobiotica
the fate of foreign compounds in biological systems
Volume 25, 1995 - Issue 7
35
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Original Article

Haemoprotein-mediated metabolism of enamines and the possible involvement of one-electron oxidations

, , , , &
Pages 769-775 | Received 10 Dec 1994, Published online: 27 Aug 2009
 

Abstract

1. Microsomal metabolism of 1-benzylpiperidine (1-BP), its cis-2,6-dimethyl (cis-2,6-DMBP), 4,4-dimethyl (4,4-DMBP), and α,α-dimethyl (α,α-DMBP) analogues, and phencyclidine (PCP) has been studied to assess the involvement of P450 oxidation of the enamine tautomers of the initial endocyclic iminium metabolites.

2. The selective prevention by cyanide of the metabolite production of 1-benzyl-3-piperidone but not 1-benzyl-3-piperidinol from 1-BP is consistent with the enamine as the source of the 3-one metabolite.

3. The parent amines and particularly the independently prepared iminium species induced a pattern of metabolism-dependent irreversible inactivation of P450 benzphetamine demethylase activity, consistent with involvement of enamine C-3 oxidation in the inactivation process.

4. Substrate activity of the endocyclic enamines and α-aminoketones (presumably the enol-enamine tautomers) for horseradish peroxidase under conditions where simple aliphatic amines display no activity is consistent with metabolic one-electron oxidations of the enamines.

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