Generation and fate of enamines in the microsomal metabolism of cyclic tertiary amines.
Biochem Biophys Res Commun
; 179(3): 1368-76, 1991 Sep 30.
Article
em En
| MEDLINE
| ID: mdl-1930182
ABSTRACT
Microsomal oxidation of 1-benzylpiperidine (1-BP) and its cis-2,6-dimethyl analog was studied to assess the involvement of endocyclic enamines, in equilibrium with the initially formed iminiums, in the metabolic activation of cyclic tertiary amines such as phencyclidine. Since the iminiums can be trapped with cyanide, the selective prevention by cyanide of the metabolic production of 1-benzyl-3-piperidone from 1-BP implicates the iminium in equilibrium with enamine as the source of this metabolite. In cases where iminium-enamine coupling is sterically prevented, the iminium in equilibrium with enamine species can be studied independently and are found to be more potent metabolism-dependent inactivators of cytochrome P-450 than are the corresponding parent amines. Possible mechanisms for biological oxidation of cyclic enamines to reactive intermediates are considered.
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Base de dados:
MEDLINE
Assunto principal:
Microssomos Hepáticos
/
Sistema Enzimático do Citocromo P-450
/
Aminas
Limite:
Animals
Idioma:
En
Revista:
Biochem Biophys Res Commun
Ano de publicação:
1991
Tipo de documento:
Article