Low level determination of p-toluenesulfonate and benzenesulfonate esters in drug substance by high performance liquid chromatography/mass spectrometry

Development and validation of GC–MS method for the determination of methyl methanesulfonate and ethyl methanesulfonate in imatinib mesylate

“…methyl methanesulfonate (MMS) [1] and ethyl methanesulfonate (EMS) [2] in pharmaceuticals have attracted the attention of regulatory authorities because these are known carcinogens and genotoxins [3]. Their presence in the pharmaceuticals is due to the formation of by-products resulting from the reaction between methanesulfonic acid (MSA) which is used as a counter ion in drug molecule and methanol or ethanol used as a solvent in the manufacturing process.…”

Development and validation of an automated static headspace gas chromatography–mass spectrometry (SHS-GC–MS) method for monitoring the formation of ethyl methane sulfonate from ethanol and methane sulfonic acid

“…Direct analysis of alkyl esters of methanesulfonates by gas chromatography (GC) was used by Ramijt et al [6] and Li [7], respectively in combination with mass spectrometric (MS) and flame ionization (FID) detection. Although ppm (g/g) sensitivity was obtained, direct injection of sulfonates in API matrix can lead to inlet contamination and/or solute degradation [7,8]. In addition, we also observed occasional formation of sulfonate esters in heated inlet systems (through sample pyrolysis and flash reaction with solvents).…”

“…As an alternative to gas chromatography, liquid chromatography (HPLC) methods have also been developed for the analysis of alkyl and aryl sulfonate esters [8]. Although thermal decomposition of the API is less likely to occur, reaction between alcohols (in the mobile phase or solvent) and trace levels of acids (present as impurities in the API or intermediate) could potentially lead to formation of sulfonate esters and consequently to false positive results.…”

Rapid Determination of Trifluoromethanesulfonate and p-Toluenesulfonate by Ion-Pair Chromatography Using a Reversed-Phase Silica-Based Monolithic Column: Application to the Analysis of Ionic Liquids

“…p-Toluenesulfonate is widely used as a stabilizer of polyreaction and a catalyst of organic esters in synthesis of medicine and pesticide. The interrelated analyses of p-toluenesulfonate to be reported mainly involve capillary electrophoresis (CE) [18] and high-performance liquid chromatography-mass spectrum [19]. Rapid and simultaneous determinations of trifluoromethanesulfonate and p-toluenesulfonate were not reported before.…”