Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume
47, Number 5, May/June 2009, pp. 359-364
GC–MS Evaluation of a Series of Acylated
Derivatives of 3,4-Methylenedioxymethamphetamine
Tarek Belal1, Tamer Awad2,
C. Randall Clark2,
and Jack DeRuiter2 1Department of Pharmaceutical Analytical Chemistry, Faculty of
Pharmacy, Alexandria University, Alexandria 21521, Egypt; 2Department
of Pharmacal Sciences, Harrison School of Pharmacy, Auburn University,
Auburn, AL 36849
A series of acylated derivatives of 3,4-methylenedioxy-methamphetamine
(3,4-MDMA) are prepared and evaluated in gas chromatography–mass
spectrometry (GC–MS) studies. The perfluoroalkyl amides
of 3,4-MDMA show the lowest GC retention, while the aromatic
amides such as the benzamide show the greatest retention on the
dimethylpolysiloxane stationary phase (Rtx-1). The mass spectral
properties of the acetyl, propionyl, and butyryl derivatives
all show a base peak at m/z 58 which is the base peak
for the underivatized 3,4-MDMA. All acylated derivatives provide
mass spectral information (m/z 162) to identify the
three-carbon side chain for 3,4-MDMA. The perfluoroalkyl amides
yield several unique mass spectral fragments for specific identification
of 3,4-MDMA. MS fragmentation pathways are illustrated and validated
using analogous deuterated derivatives. A combination of excellent
chromatographic properties and unique mass spectral fragments
allows the perfluoroalkyl amides to provide maximum specific
structural information in the GC–MS analysis of 3,4-MDMA.
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