Urinary Excretion Profiles of 2,5-Dimethoxy-4-alkylthiophenethylamine Analogs in Rats.

In rats, the urinary metabolic profiles of three hallucinogenic compounds—2C-T-2, 2C-T-4, and 2C-T-7—differed after oral administration. The major metabolite for 2C-T-7 was a β-hydroxylated-N-acetylated-sulfoxide, while for 2C-T-2 it was the N-acetylated-sulfoxide, and for 2C-T-4 the S-methylated-N-acetylated-sulfoxide predominated. These distinct metabolic patterns suggest that each analog undergoes unique biotransformation pathways.

Study at a glance

Abstract

The urinary metabolic profiles of three hallucinogenic 2,5-dimethoxy-4-alkylthiophenethylamine analogs: 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2), 2,5-dimethoxy-4-isopropylthiophenethylamine (2C-T-4), and 2,5-dimethoxy-4-propylthiophenethylamine (2C-T-7), were investigated in rats. For each drug, four male Sprague-Dawley rats were orally administered 10 mg/kg of 2C-T-2, 2C-T-4, or 2C-T-7, and urine was collected 0-24 and 24-48 h after administration. The urine samples were processed by liquid-liquid extraction, and the extracts were analyzed by liquid chromatography/mass spectrometry to quantify the metabolites. The metabolic patterns of these drugs were different: for 2C-T-7, the principal metabolite was the β-hydroxylated-N-acetylated-sulfoxide, whereas for 2C-T-2 and 2C-T-4 the major metabolites were the N-acetylated-sulfoxide and S-methylated-N-acetylated-sulfoxide, respectively.