New designer drug 4-iodo-2,5-dimethoxy-β-phenethylamine (2C-I): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric and capillary electrophoretic/mass spectrometric techniques

Studies are described on the metabolism and the toxicological analysis of the phenethylamine‐derived designer drug 4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine (2C‐I) in rat urine using gas chromatographic/mass spectrometric (GC/MS) techniques, and for a particular question, using capillary electrophoretic...

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Bibliographic Details
Published in:Journal of mass spectrometry. 2006-07, Vol.41 (7), p.872-886
Main Authors: Theobald, Denis S., Pütz, Michael, Schneider, Erhard, Maurer, Hans H.
Format: Article
Language:English
Subjects:
2C-I
4-iodo-2
4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine
5-dimethoxy-β-phenethylamine
Analytical chemistry
Animals
Biological and medical sciences
Capillary Action
CE/MS/MS
Chemistry
Chromatographic methods and physical methods associated with chromatography
Designer Drugs - isolation & purification
Designer Drugs - metabolism
Dimethoxyphenylethylamine - analogs & derivatives
Dimethoxyphenylethylamine - isolation & purification
Dimethoxyphenylethylamine - urine
Drug addictions
Electrophoresis - methods
Exact sciences and technology
Gas chromatographic methods
Gas Chromatography-Mass Spectrometry - methods
GC/MS
Male
Mass Spectrometry - methods
Medical sciences
metabolism
Other chromatographic methods
Rats
Rats, Wistar
Toxicology
urinalysis
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Summary:Studies are described on the metabolism and the toxicological analysis of the phenethylamine‐derived designer drug 4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine (2C‐I) in rat urine using gas chromatographic/mass spectrometric (GC/MS) techniques, and for a particular question, using capillary electrophoretic/mass spectrometric (CE/MS) techniques. The identified metabolites indicated that 2C‐I was metabolized on the one hand by O‐demethylation in position 2 and 5, respectively, followed either by N‐acetylation or by deamination with subsequent oxidation to the corresponding acid or reduction to the corresponding alcohol, respectively. The latter metabolite was hydroxylated in β‐position and further oxidized to the corresponding oxo metabolite. On the other hand, 2C‐I was metabolized by deamination with subsequent oxidation to the corresponding acid or reduction to the corresponding alcohol, respectively. 2C‐I and most of its metabolites were partially excreted in conjugated form. The authors' systematic toxicological analysis (STA) procedure using full‐scan GC/MS after acid hydrolysis, liquid–liquid extraction and microwave‐assisted acetylation allowed the detection of an intake of a dose of 2C‐I in rat urine that corresponds to a common drug users' dose. Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of 2C‐I in human urine. Copyright © 2006 John Wiley & Sons, Ltd.
ISSN:1076-5174
1096-9888
DOI:10.1002/jms.1045