Biological conversion of N-phenyl-2-naphthylamine to 2-naphthylamine in the Sprague-Dawley rat

Drug Chem Toxicol. 1983;6(3):295-309. doi: 10.3109/01480548309017820.


The metabolism of a widely used plastic and rubber antioxidant, N-Phenyl-2-Naphthylamine, was investigated in Sprague-Dawley rats. After repeated oral administration of this compound, urine and feces were collected for several days and analyzed for the presence of metabolites. Identification techniques included a preliminary clean-up followed by thin-layer chromatography of amines and gas chromatography-mass spectrometry of their hexafluoroacyl derivatives (HFBA). The compounds identified in both urine and feces were characterized as N-Phenyl-2-Naphthylamine (PBNA) and 2-Naphthylamine (BNA). Data obtained on urinary excretion of BNA seem to indicate that repeated administration of PBNA enhances its own metabolism.

MeSH terms

  • 2-Naphthylamine / analogs & derivatives
  • 2-Naphthylamine / metabolism*
  • Animals
  • Chromatography, Gas
  • Chromatography, Thin Layer
  • Male
  • Mass Spectrometry
  • Naphthalenes / metabolism*
  • Rats
  • Rats, Inbred Strains


  • Naphthalenes
  • neozone
  • 2-Naphthylamine