New designer drug 2,5-dimethoxy-4-ethylthio-β-phenethylamine (2C-T-2): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry

✍ Scribed by Denis S. Theobald; Roland F. Staack; Michael Puetz; Hans H. Maurer

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 393 KB
• Volume: 40
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/jms.890

✦ Synopsis

Abstract

Studies are described on the metabolism and the toxicological analysis of the phenethylamine‐derived designer drug 2,5‐dimethoxy‐4‐ethylthio‐β‐phenethylamine (2C‐T‐2) in rat urine using gas chromatography/mass spectrometry (GC/MS) after enzymatic cleavage of conjugates, liquid‐liquid extraction and derivatization. The structures of 14 metabolites were assigned tentatively by detailed interpretation of their mass spectra. Identification of these metabolites indicated that 2C‐T‐2 was metabolized by sulfoxidation followed by N‐acetylation and either hydroxylation of the S‐ethyl side chain or demethylation of one methoxy group, O‐demethylation of the parent compound followed by N‐acetylation and sulfoxidation, deamination followed by reduction to the corresponding alcohol followed by partial glucuronidation and/or sulfation or by oxidation to the corresponding acid followed either by partial glucuronidation or by degradation to the corresponding benzoic acid derivative followed by partial glucuronidation. Furthermore, 2C‐T‐2 was metabolized by N‐acetylation of the parent compound followed either by O‐demethylation and sulfoxidation or by S‐dealkylation, S‐methylation and sulfoxidation. The authors' systematic toxicological analysis (STA) procedure using full‐scan GC/MS after acid hydrolysis, liquid‐liquid extraction microwave‐assisted acetylation allowed the detection of an intake of a dose of 2C‐T‐2 in rat urine, which corresponds to a common drug users' dose. Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of 2C‐T‐2 in human urine. Copyright © 2005 John Wiley & Sons, Ltd.