Investigation and identification of the bromination products of dimethoxyamphetamines

The qualitative analysis of the aromatic bromination products of the 6 isomeric dimethoxyamphetamines and their hydrochloride or hydrobromide salts is described. Their ultraviolet, mass, and proton magnetic resonance spectra are not sufficiently different for distinction but infrared spectra allow a positive identification to be made and reference spectra are provided for the bromination products of 2,4-, 2,5-, 2,6-, 4,5-, and 3,5-dimethoxyamphetamines. The application of gas-liquid and thin layer chromatography for the analysis of these products is discussed. The bromination of 2,3-dimethoxyamphetamine consistently gave mixtures which could not be separated satisfactorily; spectra are included for completeness of the comparison of products.