Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS)

A reliable and accurate GC-MS method was developed that allows both mass spectrometric and chromatographic discrimination of the six aromatic positional isomers of trimethoxyamphetamine (TMA). Regardless of the trifluoroacetyl (TFA) derivatization, chromatographic separation of all the investigated...

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Bibliographic Details
Published in:Journal of mass spectrometry. 2008-04, Vol.43 (4), p.528-534
Main Authors: Zaitsu, Kei, Katagi, Munehiro, Kamata, Hiroe, Kamata, Tooru, Shima, Noriaki, Miki, Akihiro, Iwamura, Tatsunori, Tsuchihashi, Hitoshi
Format: Article
Language:English
Subjects:
Amphetamines - analysis
Amphetamines - chemistry
Biological and medical sciences
designer drug
Designer Drugs - analysis
Designer Drugs - chemistry
Drug addictions
Drug Evaluation, Preclinical - instrumentation
Drug Evaluation, Preclinical - methods
Drug Evaluation, Preclinical - standards
forensic science
gas chromatography-mass spectrometry
Gas Chromatography-Mass Spectrometry - methods
Gas Chromatography-Mass Spectrometry - standards
Humans
Isomerism
Medical sciences
psychotomimetic property
Reproducibility of Results
Toxicology
trifluoroacetyl derivatization
trimethoxyamphetamine
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Summary:A reliable and accurate GC-MS method was developed that allows both mass spectrometric and chromatographic discrimination of the six aromatic positional isomers of trimethoxyamphetamine (TMA). Regardless of the trifluoroacetyl (TFA) derivatization, chromatographic separation of all the investigated isomers was achieved by using DB-5ms capillary columns (30 m x 0.32 mm i.d.), with run times less than 15 min. However, the mass spectra of the nonderivatized TMAs, except 2,4,6-trimethoxyamphetmine (TMA-6), showed insufficient difference for unambiguous discrimination. On the other hand, the mass spectra of the TFA derivatives of the six isomers exhibited fragments with significant intensity differences, which allowed the unequivocal identification of all the aromatic positional isomers investigated in the present study. This GC-MS technique in combination with TFA derivatization, therefore, is a powerful method to discriminate these isomers, especially useful to distinguish the currently controlled 3,4,5-trimethoxyamphetmine (TMA-1) and 2,4,5-trimethoxyamphetmine (TMA-2) from other uncontrolled TMAs. Copyright © 2007 John Wiley & Sons, Ltd.
ISSN:1076-5174
1096-9888
DOI:10.1002/jms.1347