同位体による薬物代謝の研究(第11報)ベンゼン核重水素標識l-Ephedrineの合成およびその物理化学的性質

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As a fundamental study on the applicability of a drug labeled with deuterium on benzene ring for the human metabolic studies, l-ephedrine [arom.-^2H_5] was synthesized by a reaction sequence starting with benzene [arom.-^2H_6]. Infrared (IR), nuclear magnetic resonance (NMR), and mass spectra of l-ephedrine [arom.-^2H_5] and propiophenone [arom.-^2H_5] were compared with those of the corresponding nonlabeled compounds. The bands at 700 and 750 cm^<-1>, which appear characteristically in monosubstituted benzene derivatives, disappear completely in the IR spectra of deuterated compounds, and absorptions for the aromatic C-H (3000-3100 cm^<-1>) and aromatic C=C (1600 cm^<-1> shifted completely to 2280 cm^<-1> and 1560 cm^<-1> respectively.The signal for aromatic proton in NMR spectrum is completely lacking in the deuterated samples. From these data, it was concluded that l-ephedrine [arom.-^2H_5] obtained here does not contain a perceptible amount of hydrogen on its benzene ring. Comparison of mass spectra of deuterated compounds with that of nonlabeled compounds, suggests that an intramolecular exchange reaction between deuterium on the benzene ring and hydrogen on the side chain does occur during the fragmentation process to a small but significant extent.
公益社団法人日本薬学会の論文
1974-07-25