title: Activation of methanol by hepatic postmitochondrial supernatant: formation of a condensation product with 2,4-diaminotoluene.
abstract: 2,4-Diaminotoluene, an aromatic amine hepatocarcinogen in rats and mice, reacts extensively with formaldehyde produced by the oxidation of methanol to form a single reaction product. Using 1H and 13C NMR and high-resolution mass spectroscopy, this product was shown to be bis(2,4-diamino-5-tolyl)methane. This reaction product is shown to occur under conditions whereby methanol is metabolized to formaldehyde by rat hepatic postmitochondrial supernatant. These results demonstrate a novel reaction of aromatic amines and formaldehyde in biological samples and indicate that methanol as a solvent may become activated in vitro and produce complex interactions with solutes.
authors: Experimental Toxicology Branch, National Institute of Environmental Health Sciences, Research Triangle Park, North Carolina 27709.
authors: M L
authors: ML
authors: Cunningham
authors: H B
authors: HB
authors: Matthews
authors: L T
authors: LT
authors: Burka
mesh_terms: D000818:Animals; D001711:Biotransformation; D002457:Cell Extracts; D002851:Chromatography, High Pressure Liquid; D005557:Formaldehyde / Q000378:metabolism; D007700:Kinetics; D008099:Liver / Q000378:metabolism; D000432:Methanol / Q000493:pharmacokinetics*; D008930:Mitochondria, Liver / Q000378:metabolism*; D010655:Phenylenediamines / Q000378:metabolism*; D051381:Rats
chemical_list: D002457:Cell Extracts; D010655:Phenylenediamines; D005557:Formaldehyde; C010914:2,4-diaminotoluene; D000432:Methanol