Mechanism of Decomposition of N-Hydroxyacetaminophen, a Postulated Toxic Metabolite of Acetaminophen

Article abstract of DOI:10.1021/jm00177a019

The decomposition of N-hydroxyacetaminophen (N-acetyl-N-hydroxy-p-aminophenol, 2) a postulated toxic metabolite of acetaminophen (N-acetyl-p-aminophenol, 1) in aqueous solution is quantitatively accounted for by the appearance of equimolar amounts of p-nitrosophenol and acetaminophen.The rate of decomposition depends on initial concentration and varies with pH.Antioxidants decrease the rate of decomposition and change the products.In the presence of cysteine, N-acetyl-3-(S-cysteine)-p-aminophenol, an in vivo metabolite of acetaminophen, is a product of decomposition.