Studies on isometheptene metabolism. Identification and stereochemistry of a major metabolite isolated from rat urine.
By gas chromatography-mass spectrometry of both underivatized samples and N-acetates, the major urinary metabolite of the antispasmodic drug (+/-)-isometheptene in the rat was identified as trans-2-methyl-6-methylamino-2-hepten-1-ol. The structure and stereochemistry of the metabolites was confirmed by comparing the properties of its N-acetate with those of an authentic sample of the N-acetate of trans-2-methyl-6-methylamino-2-hepten-1-ol which was obtained by a stereospecific trans-allylic hydroxylation of isometheptene acetate with selenium dioxide in ethanol. cis-2-Methyl-6-methylamino-2-hepten-1-ol was identified as a minor urinary metabolite of isometheptene in the rat.
D000475:Alkenes / Q000652:urine; D000588:Amines / Q000652:urine*; D000818:Animals; D002849:Chromatography, Gas; D008297:Male; D013058:Mass Spectrometry; D008744:Methylamines; D010276:Parasympatholytics / Q000378:metabolism / Q000652:urine; D051381:Rats; D013237:Stereoisomerism
D000475:Alkenes; D000588:Amines; D008744:Methylamines; D010276:Parasympatholytics; C008192:isometheptene