Identification and synthesis of a methylated catechol metabolite of glutethimide isolated from biological fluids of overdose victims.
Urine samples from victims severely intoxicated by glutethimide were hydrolyzed enzymatically. TLC, GLC, and mass spectral analyses revealed a methylated catechol metabolite of the parent drug. Two synthetic pathways are described for the preparation of 2-ethyl-2-(3-methoxy-4-hydroxyphenyl)glutarimide and 2-ethyl-2-(3-hydroxy-4-methoxyphenyl)glutarimde. Comparisons of GLC and mass spectral data to a compound isolated from the body fluids of glutethimide overdose victims conclusively identified a new 3-methoxy-4-hydroxyphenyl metabolite of glutethimide in humans.
D002396:Catechols / Q000138:chemical synthesis / Q000652:urine*; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D005984:Glutethimide / Q000138:chemical synthesis / Q000506:poisoning* / Q000652:urine; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation
D002396:Catechols; D005984:Glutethimide