Chromatographic and spectroscopic analysis of the components present in the phenanthridinium trypanocidal agent isometamidium

Anal Bioanal Chem. 2015 Feb;407(4):1171-80. doi: 10.1007/s00216-014-8337-z. Epub 2014 Dec 17.

Abstract

The chromatographic isolation and characterisation of the four compounds present in the quaternary phenanthridine veterinary trypanocidal agent, isometamidium chloride hydrochloride (ISM), is reported. The isolated compounds were unambiguously characterised using spectroscopic (NMR, UV, IR and MS) methods as 3-amino-8-[3-(3-carbamimidoyl-phenyl)-triazenyl]-5-ethyl-6-phenylethidium (1a) and related isomers, 8-amino-3-[3-(3-carbamimidoyl-phenyl)-triazenyl]-5-ethyl-6-phenylethidium, 3,-8-diamino-7-[3-(3-carbamimidoyl-phenyl)-triazenyl]-5-ethyl-6-phenylethidium and 3,-8-bis[3-(3-carbamimidoyl-phenyl)-triazenyl]-5-ethyl-6-phenylethidium. During the course of this study, it was realised that the nature of the solvent used in the NMR study was critical as in DMSO-d6 the quaternary group in the compounds was reduced to dihydro forms (e.g. 2a).

MeSH terms

  • Chromatography, High Pressure Liquid / methods*
  • Dimethyl Sulfoxide / chemistry
  • Isomerism
  • Magnetic Resonance Spectroscopy / methods*
  • Mass Spectrometry / methods*
  • Molecular Structure
  • Phenanthridines / analysis*
  • Phenanthridines / chemistry
  • Quaternary Ammonium Compounds / analysis*
  • Quaternary Ammonium Compounds / chemistry
  • Solvents / chemistry
  • Spectrophotometry, Ultraviolet / methods*
  • Trypanocidal Agents / analysis*
  • Trypanocidal Agents / chemistry

Substances

  • Phenanthridines
  • Quaternary Ammonium Compounds
  • Solvents
  • Trypanocidal Agents
  • isometamidium chloride
  • Dimethyl Sulfoxide