Determination of N-methyl-1,3-propanediamine in bovine muscle by liquid chromatography with triple quadrupole and ion trap tandem mass spectrometry detection

Morantel, pyrantel and their drug-related metabolites in food of animal-origin are regulated as sum of residues which may be hydrolysed to N-methyl-1,3-propanediamine (NMPA). In this study, an isotope dilution liquid chromatography tandem mass spectrometry (LC–MS/MS) method with pentafluoropropionic acid anhydride (PFPA) derivatization was developed for the determination of NMPA in bovine muscle. A stable isotope labeled internal standard N-methyl-d3-3,3′-d2-propane-1,3-diamine (NMPA-d5) was synthesized as internal standard. NMPA was derivatized with PFPA to form an N,N′-bis (pentafluoroacyl) derivative (NMPA-PFPA) and analyzed by liquid chromatography triple quadrupole mass spectrometry (LC-QqQ-MS/MS) and liquid chromatography ion trap mass spectrometry (LC-IT-MS/MS) using negative ion electrospray ionization (ESI). Chromatographic behavior of several perfluorocarboxylic acid anhydride derivatives of NMPA and other structurally related diamines on C-18 and perfluorophenyl (PFP) columns was studied. Conversion of the parent drugs to NMPA under various hydrolysis conditions was evaluated. In addition, comparison of the matrix effect and linearity with isotopically labeled internal standard (I.S.) and analogous I.S. were performed and investigated. The method was validated using fortified bovine muscle samples. The apparent recovery (obtained after correction with an isotopically labeled I.S.) was between 89% and 97% and repeatability was less than 10%. The lowest LOD and LOQ (0.42 and 1.39 μg/kg, respectively) were obtained with LC-QqQ-MS/MS.

► Pentafluoropropionic acid anhydride as derivatization reagents for N-alkyl-1,3-propanediamine.
► Liquid chromatography tandem mass spectrometry for sensitive detection of N-methyl-1,3-propanediamine after derivatization.
► Determination of morantel, pyrantel and related metabolites in bovine muscle.