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Synthesis and Analytical Profiles for Regioisomeric and Isobaric Amines Related to MDMA, MDEA and MBDB: Differentiation of Drug and Non-Drug Substances of Mass Spectral Equivalence

NCJ Number
Date Published
October 2011
301 pages
The broad aim of this research was to improve specificity in the analytical methods used to identify MDMA, MBDB, MDEA, and related phenethylamine controlled substances.
This project has developed methods for discriminating between the methylenedioxyphen-ethylamine drugs and those regioisomeric and isobaric molecules having the same molecular weight and major fragments of equivalent mass (i.e., identical mass spectra). The project has emphasized those analytical methods commonly used in forensic laboratories for confirmation of drug identity: gas chromatography (GC), mass spectrometry (MS), and infrared spectrometry. When there are compounds that produce the same mass spectrum as the drug of interest, the identification by GC-MS must be based entirely on the ability of the chromatographic system to resolve these substances. The initial phase of this work involved the organic synthesis of the direct regioisometric substances related to MDMA, MBDB, and MDEA. Also prepared were representative samples of the indirect regioisomeric molecules and the isobaric substances, compounds of the same nominal mass but different elemental composition. Additional compounds were prepared in related categories in order to further refine the developed analytical methods and confirm/challenge experimental observation. A number of deuterium labeled analogs had been prepared to establish mass spectral fragmentation patterns. Other isomeric series were prepared for the MDMA and MBDB side chain series and the 2-, 3-, and 4-ethoxyphenyl compounds for the MBDB series. Overall, just over 90 phenethylamines having a regioisomeric or isobaric relationship to MDMA or MBDB have been synthesized and evaluated. The chromatographic retention properties for each series of isomers have been evaluated by GC techniques on a variety of stationary phases, synthesized, and evaluated. These studies established structure-retention relationship (elution orders) for the side chain regioisomers and the isobaric amines on a number of stationary phases. Extensive figures and 67 references
Date Published: October 1, 2011