[Isolation and structure determination of metabolites of xantinol from rat urine (author's transl)].
In the urine of rats as metabolites of the theophylline-derivative 7-[2-hydroxy - 3 - (N-methyl-N-2-hydroxyethyl)-amino-propyl]-1,3-dimethylxanthine (xantinol), the two stereoisomeric 2-coffeinyl-N-methyl-6-hydroxy-morpholines were found. These compounds represented about 7 to 8 percent of the eliminated xantinol and can be described structurally as semiacetals of a terminal aldehyde formed from Xantinol. Their structure has been elucidated by combined NMR- and mass-spectrometry. After oral application of xantinol-nicotinate in therapeutic doses to male test subjects, the same substances were detected by thin-layer chromatography. Both compounds could be synthetized by treatment of 7-[2,3-epoxypropyl]-theophylline or 7-[2-hydroxy-3-chloro-propyl]-theophylline with methylami-noacetaldehyde-dimethylacetal and subsequent hydrolysis of the reaction product with hydrochloric acid.
D000818:Animals; D002855:Chromatography, Thin Layer; D005260:Female; D006801:Humans; D008297:Male; D008968:Molecular Conformation; D051381:Rats; D013057:Spectrum Analysis; D013806:Theophylline / Q000031:analogs & derivatives* / Q000652:urine; D014970:Xanthines / Q000138:chemical synthesis; D014971:Xanthinol Niacinate / Q000652:urine
D014970:Xanthines; D014971:Xanthinol Niacinate; D013806:Theophylline
Isolierung und Strukturermittlung der Metaboliten von Xantinol aus dem Urin der Ratte