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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

N-hydroxyphenacetin, a new urinary metabolite of phenacetin in the rat.

N-Hydroxyphenacetin has been found in the urine of rats dosed with phenacetin, extending previous reports that phenacetin is N-hydroxylated by liver microsomes in vitro. After an oral dose of phenacetin (500 mg/kg) urine was collected for 24 hr, conjugates hydrolyzed with extract of Helix pomatia, and the metabolites extracted with dichloromethane and treated with diazomethane. Methylation of N-hydroxyphenacetin produced a stable derivative, N-methoxyphenacetin, which was separated from most other metabolites by thin layer chromatography. Identification of N-methoxyphenacetin was by combined gas chromatography-mass spectrometry and comparison with the synthetic reference compound. Quantification by gas chromatography with flame-ionization detection showed that 0.023% of the dose phenacetin was recovered from urine as N-hydroxyphenacetin. It is probable that this value considerably underestimates the extent of phenacetin N-hydroxylation in vivo, inasmuch as N-hydroxyphenacetin is known to be rapidly degraded in biological systems.[1]


  1. N-hydroxyphenacetin, a new urinary metabolite of phenacetin in the rat. McLean, S., Davies, N.W., Watson, H., Favretto, W.A., Bignall, J.C. Drug Metab. Dispos. (1981) [Pubmed]
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