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New designer drugs N ‐(1‐phenylcyclohexyl)‐2‐ethoxyethanamine (PCEEA) and N ‐(1‐phenylcyclohexyl)‐2‐methoxyethanamine (PCMEA): Studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques
Author(s) -
Sauer Christoph,
Peters Frank T.,
Staack Roland F.,
Fritschi Giselher,
Maurer Hans H.
Publication year - 2008
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1312
Subject(s) - chemistry , hydroxylation , urine , designer drug , metabolite , phencyclidine , chromatography , metabolism , gas chromatography–mass spectrometry , stereochemistry , mass spectrometry , organic chemistry , biochemistry , enzyme , pharmacology , drug , receptor , medicine , nmda receptor
Abstract Studies are described on the metabolism and the toxicological detection of the phencyclidine‐derived designer drugs N ‐(1‐phenylcyclohexyl)‐2‐ethoxyethanamine (PCEEA) and N ‐(1‐phenylcyclohexyl)‐2‐methoxyethanamine (PCMEA) in rat urine using gas chromatographic/mass spectrometric (GC/MS) techniques. The identified metabolites indicated that PCEEA and PCMEA were transformed to the same metabolites by N ‐dealkylation and O ‐dealkylation partially followed by oxidation of the resulting alcohol to the respective carboxylic acid and hydroxylation of the cyclohexyl ring at different positions and combinations of those. Finally, aromatic hydroxylation of the O ‐dealkylated metabolites was partially followed by hydroxylation of the cyclohexyl ring at different positions. All 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 common drug users' dose both of PCEEA and PCMEA in rat urine. Assuming similar metabolism in humans, the STA should be suitable for proof of an intake of PCEEA and PCMEA in human urine, although their differentiation is not possible due to common metabolites. Copyright © 2007 John Wiley & Sons, Ltd.