Published:Journal of Chromatographic Science,
ISSN 0021-9665Volume
41, Number 5, May/June 2003, pp 227-233
Chromatographic and Spectroscopic Methods of Identification
for the Side-Chain Regioisomers of 3,4-Methylenedioxyphenethylamines Related
to MDEA, MDMMA, and MBDB
Laura Aalberg[1],[2], Jack DeRuiter[1], F. Taylor Noggle[3],
Erkki Sippola[2], and C. Randall Clark[1]
[1]Department of Pharmacal Sciences, School of Pharmacy, Auburn University,
Auburn, AL 36849;
[2]National Bureau of Investigation Crime Laboratory, 01370
Vantaa,
Finland; and
[3]Alabama Department of Forensic Sciences, Wire Road, Auburn,
AL 36830
Three regioisomeric 3,4-methylenedioxyphenethylamines having
the same molecular weight and major mass spectral fragments of equivalent mass
have been reported as components of clandestine drug samples in recent years.
These drugs of abuse are 3,4-methylenedioxy-N-ethylamphetamine, 3,4-methylenedioxy-N,
N-dimethylamphetamine, and N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine.
These three compounds are a subset of a total of ten regioisomeric 3,4-methylenedioxyphenethylamines
of molecular weight 207, yielding regioisomeric fragment ions of equivalent
mass (m/z 72 and 135/136) in the electron impact mass spectrum. The specific
identification of one of these compounds in a forensic drug sample depends
upon the analyst’s ability to eliminate the other regioisomers as possible
interfering or coeluting substances. This paper reports the synthesis, mass
spectral characterization, and chromatographic analysis of these ten unique
regioisomers. The ten regioisomeric methylenedioxyphenethylamines are synthesized
from commercially available precursor chemicals. The electron impact mass spectra
of these regioisomers show some variation in the relative intensity of the
major ions with only one or two minor ions that might be considered side-chain
specific fragments. Thus, the ultimate identification of any one of these amines
with the elimination of the other nine regioisomeric substances depends heavily
upon chromatographic methods. Chromatographic separation of these ten uniquely
regioisomeric amines is studied using gas chromatographic temperature program
optimization.
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