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  • Title: [Isolation and structure determination of metabolites of xantinol from rat urine (author's transl)].
    Author: Tauscher M, Eckhardt G, Geisel B, Credner K.
    Journal: Arzneimittelforschung; 1976; 26(7):1342-4. PubMed ID: 1036921.
    Abstract:
    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.
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