title: Chromatographic and spectroscopic analysis of the components present in the phenanthridinium trypanocidal agent isometamidium.
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).
authors.affiliation: Pharmaceutical Sciences Group, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, G4 0RE, Scotland.
authors.forename: John O
authors.initials: JO
authors.lastname: Igoli
authors.forename: Gavin
authors.initials: G
authors.lastname: Blackburn
authors.forename: Alexander I
authors.initials: AI
authors.lastname: Gray
authors.forename: Oliver B
authors.initials: OB
authors.lastname: Sutcliffe
authors.forename: David G
authors.initials: DG
authors.lastname: Watson
authors.forename: Melvin R
authors.initials: MR
authors.lastname: Euerby
authors.forename: Graham G
authors.initials: GG
authors.lastname: Skellern
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry / Q000379:methods*; D015394:Molecular Structure; D010617:Phenanthridines / Q000032:analysis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000032:analysis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet / Q000379:methods*; D014344:Trypanocidal Agents / Q000032:analysis* / Q000737:chemistry
chemical_list: D010617:Phenanthridines; D000644:Quaternary Ammonium Compounds; D012997:Solvents; D014344:Trypanocidal Agents; C000702:isometamidium chloride; D004121:Dimethyl Sulfoxide