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The brominated products from all six positional isomers of dimethoxyphenethylamine are prepared, and their analytical properties are evaluated. The major bromination product from 3,5-dimethoxyphenethylamine is the 2,6-dibromo isomer; all other regioisomers of dimethoxyphenethylamine yield a monobromo species as the major product. The mass spectra divide these compounds into two distinct groups: one group showing a strong  m/z  180 ion via loss of bromine from the molecular ion (M-Br) †  and a second group showing no significant  m/z  180 ion. The three compounds that do not show the  m/z  180 ion in their electron-impact mass spectra are brominated 2,4-; 2,5-; and 2,6-dimethoxyphenethylamine. These compounds are well-resolved by reversed-phase liquid chromatographic methods using a Hypersil Elite C 18  stationary phase and a mobile phase of phosphate buffer (pH 3) and methanol—acetonitrile.

journal of chromatographic science

Gas Chromatographic—Mass Spectrometric and High-Performance Liquid Chromatographic Analyses of the Bromination Products of the Regioisomeric Dimethoxyphenethylamines: Differentiation of Nexus from Five Positional Isomers