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Electrochemical mass spectrometric studies on 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine



Electrochemical mass spectrometric studies on 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine



Rapid Communications in Mass Spectrometry 22(13): 2089-2096



Mechanistic studies on chemical and biological one-electron oxidations of cyclic tertiary allylamines are being pursued with the aid of an electrochemical-electrospray ionization mass spectrometric based assay. The results of previous studies on the electrochemical oxidation of 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine have documented a two-electron oxidative N-decyclopropylation pathway. The present paper describes the characterization of a second pathway involving an overall four-electron oxidation of this cyclopropylamine. The results document more completely the fate of cyclopropylaminyl radical cations that are thought to be intermediates in enzyme-catalyzed oxidations of aminyl substrates and that may lead to chemically reactive metabolites.

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Accession: 031210432

Download citation: RISBibTeXText

PMID: 18523979

DOI: 10.1002/rcm.3592


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