Liquid Chromatographic and Mass Spectral Analysis of 1-Phenyl-3-Butanamines: Homologues of the Amphetamines

Abstract

The N-substituted 1-phenyl-3-butanamines were prepared from 1-phenyl-3-butanone (benzylacetone) via reductive amination. the 3-butanamines are homologues of the amphetamines, a series of popular drugs of abuse. the N-substituted 3-butanamines were separated via reversed-phase liquid chromatography using an acidic mobile phase (pH 3) and a phenyl silica stationary phase. Similar reversed-phase conditions were used to separate the primary amine homologues amphetamine and 1-phenyl-3-butanamine, and the secondary amine homologues methamphetamine and N-methyl-1-phenyl-3-butanamine. the mass spectra (EI) for the 3-butanamines show the characteristic imine base peaks which are identical to those for the N-substituted amphetamines making these two series of compounds very similar by EI fragmentation. the major difference between compounds from the two series possessing identical N-substitutents is the mass of the molecular ion.