The role of iminium-enamine species in the toxication and detoxication of cyclic tertiary amines.

Abstract

Aliphatic cyclic tertiary amines constitute a major class of naturally occurring and synthetic drugs directed at central biogenic amine receptors. Microsomal metabolism of these amines is known to be associated with low levels of covalent binding and/or suicide inactivation of the pertinent metabolizing P-450 isozymes; two of the more notorious examples are phencyclidine (1-(1phenylcyclohexyl)piperidine) (PCP) (Hoag et al. 1984) and nicotine (Shigenaga et al. 1988).