title: New designer drug 2,5-dimethoxy-4-ethylthio-beta-phenethylamine (2C-T-2): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry.
abstract: Studies are described on the metabolism and the toxicological analysis of the phenethylamine-derived designer drug 2,5-dimethoxy-4-ethylthio-beta-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.
authors.affiliation: Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, University of Saarland, D-66421 Homburg (Saar), Germany.
authors.forename: Denis S
authors.initials: DS
authors.lastname: Theobald
authors.forename: Roland F
authors.initials: RF
authors.lastname: Staack
authors.forename: Michael
authors.initials: M
authors.lastname: Puetz
authors.forename: Hans H
authors.initials: HH
authors.lastname: Maurer
mesh_terms: D000818:Animals; D015198:Designer Drugs / Q000493:pharmacokinetics*; D005554:Forensic Medicine / Q000379:methods; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D008297:Male; D010627:Phenethylamines / Q000493:pharmacokinetics / Q000652:urine*; D051381:Rats; D017208:Rats, Wistar; D015813:Substance Abuse Detection / Q000379:methods*; D019966:Substance-Related Disorders / Q000652:urine*
chemical_list: C487778:2,5-dimethoxy-4-n-propylthiophenethylamine; D015198:Designer Drugs; D010627:Phenethylamines