Detection of 3-hydroxy-3-methyloxindole in human urine

Life Sci. 1989;45(12):1119-26. doi: 10.1016/0024-3205(89)90169-0.

Abstract

During routine toxicological screening of urine for possible drug overdose, using two-dimensional thin-layer chromatography, an unknown substance was periodically detected that could not be related to any known drug. The substance was mass-isolated from the urine of a schizophrenic patient, who excreted it prolifically and it was chemically identified as 3-hydroxy-3-methyloxindole by mass spectrometry and 1H- and 13C-NMR. The structure was confirmed by synthesis through methylation of isatin. This is the first report associating 3-hydroxy-3-methyloxindole with human biochemistry. It is thought that this substance is an in vivo oxidation product of 3-methylindole which is a metabolic product of tryptophan, produced by bacteria in the colon.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Humans
  • Indoles / urine*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Oxindoles

Substances

  • Indoles
  • Oxindoles
  • 3-hydroxy-3-methyloxindole