Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume
46, Number 8, September 2008, pp. 671-679
GC–MS Analysis of Ring and Side Chain Regioisomers
of Ethoxyphenethylamines
Tamer Awad, Jack DeRuiter, and C. Randall Clark
Department of Pharmacal Sciences, School of Pharmacy, Auburn
University, Auburn, AL 36849
Mass spectral differentiation of 3,4-methylenedioxymethamphetamine
(3,4-MDMA), a controlled drug, and its 2,3-regioisomer from the
ring substituted ethoxyphenethylamines is possible after formation
of the perfluoroacyl derivatives, pentafluoropropionamides (PFPA),
and heptafluorobutyrylamides (HFBA). The ring substituted ethoxyphenethylamines
constitute a unique set of compounds having an isobaric relationship
with 3,4-MDMA. These isomeric forms of the 2-, 3-, and 4-ethoxy
phenethylamines have mass spectra essentially equivalent to 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.
All the side chain regioisomers of 2-ethoxy phenethylamine having
equivalent mass spectra to 3,4-MDMA are synthesized and compared
via gas chromatography–mass spectrometry to 2,3- and 3,4-methylenedioxymethamphetamine.
The mass spectra for the perfluoroacyl derivatives of the primary
and secondary amine regioisomers are significantly individualized,
and the side chain regioisomers yield unique hydrocarbon fragment
ions at m/z 148, 162, and 176. Additionally, the substituted
ethoxymethamphetamines are distinguished from the methylenedioxymethamphet-amines
via the presence of the m/z 107 ion. Gas chromatographic
separation on relatively non-polar stationary phases successfully
resolves these derivatives.
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