GC-IRD studies on regioisomeric ring substituted methoxy methyl phenylacetones related to 3,4-methylenedioxyphenylacetone

The methoxy methyl phenylacetones share an isobaric relationship (equivalent mass but different elemental composition) to the controlled precursor substance 3,4-methylenedioxyphenylacetone (3,4-methylenedioxyphenyl-2-propanone; 3,4-MDP-2-P). The ten ring substituted methoxy methyl phenylacetones are resolved by capillary gas chromatography on a modified cyclodextrin stationary phase. All ten regioisomeric ketones eluted before the controlled precursor substance 3,4-methylenedioxyphenylacetone. The vapor phase infrared spectra generated from the capillary column effluent clearly differentiated 3,4-MDP-2-P from the various methoxy methyl phenylacetones. Additionally the methoxy methyl phenylacetones provide unique individual infrared spectra. Infrared absorption frequencies and patterns confirmed the relative position of the methoxy-group and the acetone side-chain for the regioisomeric ketones.