This article reports on a project that used GC-MS to analyze acylated derivatives of a series of side chain regioisomers of 2-methoxy-4-methyl-phenethylamines.
Five side chain regioisomers of 2-methoxy-4-methylphenethylamine constitute a unique set of compounds having an isobaric relationship with the controlled drug substance 3,4-methylenedioxymethamphetamine (3,4-MDMA or Ecstasy). These isomeric forms of the 2-methoxy-4-methyl-phenethylamines have mass spectra essentially equivalent to 3,4-MDMA; all have molecular weight of 193 and major fragment ions in their electron ionization mass spectra at m/z 58 and 135/136. Mass spectral differentiation of 2,3 and 3,4-MDMA from primary and secondary amine regioisomeric side chains of 2-methoxy-4-methylphenethylamines was possible after formation of the perfluoroacyl derivatives, pentafluoropropionamides (PFPA) and heptafluorobutyrylamides (HFBA). The mass spectra for these derivatives were individualized, and the resulting unique fragment ions enabled specific side-chain identification. The individualization was the result of fragmentation of the alkyl carbon-nitrogen bond yielding unique hydrocarbon fragments of varying mass. Gas chromatographic separation on relatively non-polar stationary phases gave essentially base line resolution for these compounds. (publisher abstract modified)