Regioisomeric bromodimethoxy benzyl piperazines related to the designer substance 4-bromo-2,5-dimethoxybenzylpiperazine: GC–MS and FTIR analysis

A series of seven regioisomeric bromodimethoxy benzyl piperazines including the designer benzylpiperazine (4-bromo-2,5-dimethoxybenzylpiperazine) were synthesized and their analytical profiles evaluated using GC–MS and FT-IR. The mass spectra for the seven regioisomeric bromodimethoxy benzyl piperazines are almost identical with only the two 2,3-dimethoxy isomers showing one unique major fragment ion at m/z 214/216. Thus, mass spectrometry alone does not provide for the confirmation of identity of any one of the seven compounds to the exclusion of the other isomers. Perfluoroacylation of the secondary amine nitrogen for each of the seven regioisomers gave mass spectra showing some differences in the relative abundance of fragment ions without the appearance of any unique fragments for specific confirmation of structure. Attenuated total reflection infrared spectroscopy provides direct confirmatory data for differentiation between the seven regioisomeric aromatic ring substituted bromodimethoxy benzyl piperazines. Mixtures of the seven piperazine PFP derivatives were successfully resolved via capillary gas chromatography using a relatively polar stationary phase composed of 100% trifluoropropyl methyl polysiloxane. (Publisher abstract provided.)