Liquid Chromatographic and Mass Spectral Analysis of N-Substituted Analogues of 4-Methoxyamphetamine

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Abstract
A number of N-alkyl substituted 4-methoxyamphetamines were synthesized and characterized as potential designer drugs related to the amphetamines. These amines were prepared via reductive amination of 4-methoxyphenylacetone with appropriate alkylamines. The ultraviolet absorption properties of the compounds are very similar, displaying absorption maxima at 274 nm and absorptivities of 1.4 × 103 L/mole-cm. The amines were separated by reversed-phase liquid chromatography using an acidic aqueous acetonitrile mobile phase and several hydrocarbon stationary phases. The mass spectra of the N-alkyl analogues show an aminedominated fragmentation pattern with molecular ions of very low relative abundance. These amines can be readily distinguished from each other and other amphetamine-type compounds on the basis of their unique chromatographic and spectral properties.