Mass spectrometric structure determination of metabolites of 3-[2-(N,N-dimethylaminomethyl)phenylthio]phenol

Abstract Metabolites of 3-[2-(N,N-dimethylaminoethyl)phenylthio]phenol ( I ) were isolated from the urine of rats, mice, rabbit and dog and from the faeces of rats by extraction and thin-layer chromatography. From the mass spectrum of I and using characteristics mass shifts in the spectra of metabolites, the structures of four metabolites were determined, whereas for two other isomeric metabolites the structures were resolved by means of IR spectra. Conclusions regarding the structures derived from the spectra were confirmed by comparing them with synthetic standards. Generally, metabolic changes of I can be characterized by demethylation, hydroxylation combined with methylation, S-oxidation and by a combination of these metabolic reactions.