Nitroanilines are the reduction products of benzofuroxan system by oxyhemoglobin (HbO2 2+).
Benzofuroxans are interesting compounds which display several biochemical and pharmacological properties. Recent studies from our laboratory demonstrate that they are reduced by ferrous salts at room temperature and that the principal reaction products are o-nitroanilines. This paper shows that simple benzofuroxan derivatives are also able to oxidise HbO2 2+ to methemoglobin (MetHb3+) (UV detection) and to form o-nitroanilines (HPLC detection). From a toxicological point of view this reaction is interesting, since it indicates that the blood is a site for metabolism of these compounds with consequent methemoglobinemia and formation of toxic compounds.
Medana
C
C
Dipartimento di Scienza e Tecnologia del Farmaco, Turin, Italy.
Visentin
S
S
Grosa
G
G
Fruttero
R
R
Gasco
A
A
D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001583:Benzoxazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010108:Oxyhemoglobins / Q000737:chemistry*
D000814:Aniline Compounds; D001583:Benzoxazoles; D009574:Nitro Compounds; D010108:Oxyhemoglobins