Detection of 3-hydroxy-3-methyloxindole in human urine.
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.
Albrecht
C F
CF
Department of Pharmacology, University of Stellenbosch Medical School, Tygerberg, Republic of South Africa.
Chorn
D J
DJ
Wessels
P L
PL
D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006801:Humans; D007211:Indoles / Q000652:urine*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D000078183:Oxindoles
D007211:Indoles; D000078183:Oxindoles; C061286:3-hydroxy-3-methyloxindole