TY - JOUR T1 - THE METABOLISM OF C<sup>14</sup> 2-PAM IN THE ISOLATED PERFUSED RAT LIVER. III. 1-METHYL-2-CYANOPYRIDINIUM ION JF - Journal of Pharmacology and Experimental Therapeutics JO - J Pharmacol Exp Ther SP - 117 LP - 124 VL - 140 IS - 1 AU - James L. Way AU - Paul B. Masterson AU - James A. Beres Y1 - 1963/04/01 UR - http://jpet.aspetjournals.org/content/140/1/117.abstract N2 - Isotopically labeled 2-PAM (1-methyl-2-formylpyridinium iodide oxime-1-C14) was prepared and its metabolic disposition was investigated in the isolated perfused rat liver. Isolation of a second metabolite of 2-PAM, namely 1-methyl-2-cyanopyridinium ion, from the perfusate was accomplished by ethanol extraction, charcoal adsorption chromatography, ion exchange chromatography, paper chromatography and paper electrophoresis. The properties of this metabolite were found to be consistent with those of a 1-methyl-2-cyanopyridinium ion. Characterization of this metabolite was carried out by comparing its chemical, spectral, chromatographic and electrophoretic properties with those of authentic 1-methyl-2-cyanopyridinium ion. The alkaline hydrolytic products of the metabolite and the 2-cyanopyridinium ion were compared with cyanide ion, 1-methyl-2-carbamidopyridinium ion and 1-methyl-2-pyridone. The possible metabolic role of 2-cyanopyridinium ion as an intermediate for the conversion of 2-PAM to the 2-O-conjugate pyridinium ion and the possible reaction mechanisms involved in the conversion were considered. ER -