Electrochemical mass spectrometric studies on 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine.
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.
Department of Chemistry, Virginia Tech, Blacksburg, VA 24061-0212, USA. ncastagn@vt.edu
Neal
N
Castagnoli
Philippe
P
Bissel
Ulrik
U
Jurva
Mehdi
M
Ashraf-Khorasani
D015632:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
C078252:1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine; D015632:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine