Synthesis and identification of urinary metabolites of 4-iodo-2,5-dimethoxyphenethylamine.

After oral administration to rats, the drug 2C-I is broken down into several metabolites through O-demethylation, N-acetylation, and deamination followed by oxidation to carboxylic acid. Five of these metabolites were synthesized in the lab and identified using gas chromatography/mass spectrometry. The findings will aid forensic analysis of 2C-I and its metabolites in biological samples.

Study at a glance

Abstract

This article describes the synthesis and identification of urinary metabolites of 4-iodo-2,5-dimethoxyphenethylamine (2C-I), a new psychoactive drug. 2C-I hydrochloride was administered orally to male Sprague-Dawley rats, and the urinary extracts were analyzed by gas chromatography/mass spectrometry (GC/MS), then five putative 2C-I metabolites were synthesized in our laboratory. In the synthetic process of the 2C-I metabolites, iodination of the aromatic ring was successfully carried out using iodine and orthoperiodic acid as the iodination reagent, and selective debenzylation of aryl benzyl ether was accomplished by the acid hydrolysis method using trifluoroacetic acid and thioanisole. The synthesized metabolites were well separated and detected by GC/MS after valeryl derivatization. The results showed that 2C-I underwent O-demethylation, N-acetylation, and deamination, followed by oxidation to the corresponding carboxylic acid in rats. The data presented in this study will be very useful for the analysis of 2C-I and its metabolites in forensic samples.