Structure Analysis of the Interfering Substance N-methyl-2-phenylpropan-1-amine of Methamphetamine in Wastewater

doi:10.12116/j.issn.1004-5619.2022.320102

Abstract

Abstract:

Objective To analyze the chemical structure of the interfering substance that affects the result of methamphetamine analysis in wastewater. Methods A combination of GC-MS and liquid chromatography-quadrupole time-of-flight mass spectrometry （LC-QTOF-MS） was used to analyze the mass spectrum characteristics of the interfering substance that affects the result of methamphetamine analysis and to infer its possible structure. Liquid chromatography-triple quadrupole-mass spectrometry （LC-TQ-MS） was used to confirm the control material. Results Using LC-QTOF-MS in positive electrospray ionization （ESI⁺） mode, the mass-to-charge ratio （m/z） of quasi-molecular ion in the MS¹ mass spectrometry of interfering substance was identical to that of methamphetamine, indicating that the interfering substance was probably an isomer of methamphetamine. The MS² mass spectra obtained at three collision energies of 15 V, 30 V and 45 V were highly similar to methamphetamine, suggesting that the interfering substance contained methylamino and benzyl groups. Further analysis using GC-MS in electron impact （EI） ionization mode showed that the base peak in the mass spectrum of the interfering substance was at m/z 44. The interfering substance was confirmed to be N-methyl-2-phenylpropan-1-amine by compared with the standard reference. Conclusion The chemical structure of N-methyl-2-phenylpropan-1-amine is highly similar to methamphetamine, which is easy to cause interference for the detection of trace amounts of methamphetamine in wastewater using LC-TQ-MS. Therefore, in the actual analysis, the chromatographic retention time can be used to distinguish between N-methyl-2-phenylpropan-1-amine and methamphetamine.

Key words: forensic medicine, toxicological analysis, methamphetamine, wastewater analysis, mass spectrometry, interfering substance, N-methyl-2-phenylpropan-1-amine （phenpromethamine）

CLC Number:

DF795.1

Ting-ting ZHANG, Yu HUANG, Xue-jun ZHANG, Jie CHEN, Zhen-dong HUA. Structure Analysis of the Interfering Substance N-methyl-2-phenylpropan-1-amine of Methamphetamine in Wastewater[J]. Journal of Forensic Medicine, 2022, 38(6): 726-732.

Figures/Tables 7

Fig. 1 LC-TQ-MS chromatograms of the wastewater sample

Fig. 2 MS2 spectra of interfering substance and methamphetamine under different collision energies

Fig. 3 Extracted ion chromatograms of the sample obtained by GC-MS

Fig. 4 Chemical structures of two suspected substances

Fig. 5 MRM chromatogram obtained by LC-TQ-MS and total ion chromatogramobtained by GC-MS of three mixed reference materials

Fig. 6 EI mass spectra of three mixed reference materials （1 mg/mL） obtained by GC-MS

Fig. 7 Proposed fragmentation pathways of three mixed reference materials in EI ionization mode and ESI-CID mode

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