Five benzothiazole derivatives leached into injections by the rubber plunger-seals of disposable syringes were identified by electron impact (EI) and chemical ionization (CI) mass spectrometry. These are 2-hydroxybenzothiazole, 2-mercaptobenzothiazole, 2-(methylmercapto)benzothiazole, 2-(2-hydroxyethoxy)benzothiazole and 2-(2-hydroxyethylmercapto)benzothiazole. 2-Mercaptobenzothiazole is used as a vulcanization accelerator. The other four compounds are formed from the zinc derivative of 2-mercaptobenzothiazole during sterilization with ethylene oxide. Toxicological, technological and legal consequences of the leaching are discussed briefly.
The mass spectra of the title compounds point to rupture of S-C-2 and N-C-4 bonds as being the dominant reaction under electron impact. I3C labelling of a selected position of the ring allows some fragmentation pathways to be confirmed.
The molecular ions of tfniazole and isothiazole mainly isometize to a common structure before fragmentation, as evidenced by the analysis of metastable ions abundances and kinetic energy releases.
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