Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume
47, Number 4, April 2009, pp. 279-286
GC and Mass Spectral Studies on Acylated Side
Chain Regioisomers of 3-Methoxy-4-methyl-phenethylamine and 4-Methoxy-3-methyl-phenethylamine
Tamer Awad1, Jack DeRuiter1,
Tarek Belal2, and
C. Randall Clark1, 1Department of Pharmacal Sciences, School of Pharmacy, Auburn
University, Auburn, AL and 2Department of Pharmaceutical Analytical
Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria
21521 Egypt
The side chain regioiomers of the 3-methoxy-4-methylphenethylamines
and 4-methoxy-3-methyl-phenethylamines have mass spectra essentially
equivalent to the controlled drug substance 3,4-methylenedioxymethamphetamine
(3,4-MDMA), all have molecular weight of 193 and major fragment
ions in their electron ionization mass spectra at m/z 58
and 135/136. Furthermore, the compounds in this study have ring
substitutions in the same relative positions as 3,4-MDMA. The
nonequivalence of the substituents (methoxy and methyl) yields
two sets of compounds, 3-methoxy-4-methyl- and 4-methoxy-3-methylphenethylamines.
The perfluoroacyl derivatives (pentafluoropropionylamides and
heptafluorobutrylamides) of the primary and secondary regioisomeric
amines were prepared and evaluated in gas chromatography–mass
spectrometry studies. The mass spectra for these derivatives
are significantly individualized and the resulting unique fragment
ions allow for specific side chain identification. The heptafluorobutrylamide
derivatives offer more fragment ions than the pentafluoropropionylamides
for molecular individualization among these regioisomeric substances.
These acylated derivatives show excellent resolution on a dimethyl
polysiloxane stationary phase such as Rtx-1.
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