The gas chromatographic and mass spectrometric behavior of 2-amino-1-iodo-3-phenylpropane (iodoamphetamine)

The gas chromatographic and mass spectrometric behavior of 2-amino-1-iodo-3-phenylpropane (iodoamphetamine) was investigated. It was determined that the compound is unstable under the gas chromatographic mass spectrometric conditions used, undergoing a number of reactions and rearrangements. When iodoamphetamine hydrochloride was neutralized with base and the product examined by gas chromatography two peaks resulted. The major peak was identified as 2-benzylaziridine formed by the expulsion of HI from iodoamphetamine. The minor peak corresponded to iodoamphetamine itself. When an ethanolic solution of iodoamphetamine hydrochloride was injected into the gas chromatograph, however, three peaks were observed. Two of the three peaks had retention times identical to those identified previously. The other peak was concluded to be a chloro compound resulting from the opening of the aziridine ring with chloride ion.