Chromatographic and mass spectral studies on regioisomeric and mass equivalent derivatives related to the methylenedioxyphenethylamines

The popular drugs of abuse 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyethylamphetamine (MDEA) have regioisomeric and mass equivalent derivatives, which have similar analytical properties and thus the potential of misidentification. MDMA and MDEA were compared to regioisomeric substances by using spectrometric and chromatographic techniques. Additional studies were accomplished to evaluate the use of minor components in the MDMA dosage form to determine route of clandestine synthesis.; The direct regioisomers of MDMA and MDEA and also mass equivalent derivatives related to MDMA were synthesized. The spectrometric studies of the direct regioisomers of MDMA and MDEA that they can not be easily differentiated by mass spectrometry or ultraviolet (UV) spectrophotometry. Mass equivalent derivatives also produced very similar mass spectra, but by UV they can be distinguished from their methylenedioxyphenyl regioisomers. Chromatographic studies included both gas and liquid chromatography and DryLab optimization technique was applied. The optimum gas chromatographic separation of regioisomers of MDMA was obtained when 35% phenyl methyl silicone column was used at fast linear temperature program rates. Mass equivalent derivatives of MDMA have different elution properties than MDMA and therefore misidentification due the coelution is unlikely. The optimum separation of regioisomers of MDEA was obtained when non-polar stationary phases were used.; The optimum reversed phase liquid chromatographic separations were obtained on a bonded C18 stationary phase at low temperatures with relatively short gradient times. The optimum mobile phase composition was methanol and pH 3 phosphate buffer to separate regioisomers of MDMA, and acetonitrile and pH 3 phosphate buffer for mass equivalent derivatives of MDMA and regioisomers of MDEA.