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Metabolic studies on phencyclidine: characterization of a phencyclidine iminium ion metabolite.

Abstract：

:Studies on the metabolic bioactivation of the psychotomimetic amine phencyclidine have been pursued through the characterization of a new metabolite which is formed via initial cytochrome P-450 catalyzed oxidation of the parent drug to the corresponding iminium species. CI mass spectrometric and diode array UV and 1H NMR spectral analyses provided evidence for the conjugated amino enone compound, 1-(1-phenylcyclohexyl)-2,3-dihydro-4-pyridone. Confirmation of the proposed structure was achieved by comparing the 1H NMR and high-resolution EI mass spectral properties of the metabolic isolate with the corresponding spectra of an authentic synthetic sample. Possible intermediates involved in the formation of the dihydropyridone metabolite from the phencyclidine iminium ion are discussed in terms of structural analogies to reactive intermediates formed in the bioactivation of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP).

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Hoag MK,Schmidt-Peetz M,Lampen P,Trevor A,Castagnoli N Jr

doi

10.1021/tx00002a007

subject

Has Abstract

pub_date

1988-03-01 00:00:00

pages

128-31

issue

2

eissn

0893-228X

issn

1520-5010

journal_volume

1

pub_type

杂志文章

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