Published:Journal of Chromatographic Science,
ISSN 0021-9665Volume
38, Number 8, August 2000, pp. 329-337
Chromatographic
and Mass Spectral Methods of Identification for the Side-Chain and Ring Regioisomers
of MethylenedioxymethamphetamineLaura
Aalberg1,2, Jack DeRuiter1, F. Taylor Noggle3, Erkki Sippola2, and C. Randall
Clark1
1Department of Pharmacal Sciences, School of Pharmacy, Auburn University, Auburn,
AL 36849;
2National Bureau of Investigation, Crime Laboratory, 01300 Vantaa, Finland;
and
3Alabama Department of Forensic Sciences, Wire Road, Auburn, AL 36830
The
popular drug of abuse 3,4-methylenedioxymethamphetamine (MDMA) is one of a total
of 10 regioisomeric 2,3- and 3,4-methylenedioxyphenethylamines of MW 193 that
yields regioisomeric fragment ions with equivalent mass (m/z 58 and 135/136)
in the electron-impact (EI) mass spectrum. Thus, these 10 methylenedioxyphenethylamines
are uniquely isomeric; they have the same molecular weight and equivalent major
fragments in their mass spectra. The specific identification of one of these
compounds (i.e., Ecstasy or 3,4-MDMA) in a forensic drug sample depends upon
the analyst’s ability to eliminate the other regioisomers as possible interfering
or coeluting substances. This study reports the synthesis, chemical properties,
spectral characterization, and chromatographic analysis of these 10 unique regioisomers.
The ten 2,3- and 3,4-regioisomers of MDMA are synthesized from commercially
available precursor chemicals. In the EI mass spectra, the side-chain regioisomers
show some variation in the relative intensity of the major ions, with the exception
of only one or two minor ions that might be considered side-chain specific fragments.
The position of substitution for the methylenedioxy ring is not easily determined
by mass spectral techniques, and the ultimate identification of any one of these
amines with the elimination of the other nine must depend heavily upon chromatographic
methods. The chromatographic separation of these 10 uniquely regioisomeric amines
are studied using reversed-phase liquid chromatographic methods with gradient
elution and gas chromatographic techniques with temperature program optimization.
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