Chinese Journal of Magnetic Resonance ›› 2010, Vol. 27 ›› Issue (4): 609-616.

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NMR Characteristics and Conformational Analysis of Oxiracetam

 ZHU Chuan-Jun1,2, JIN Xiao-Feng3, JIANG Biao1*, CUI Yu-Xin4*   

  1. 1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;
    2. Shanghai Torch Innovation Park of Fine Chemical Industry Analysis Center, Shanghai 201512, China;
    3. Changzhou Pharmaceutical Factory, Changzhou 213018, China; 
    4. State Key Laboratory of Natural and Biomimetic Drugs (Peking University), Beijing 100191, China
  • Received:2009-11-02 Revised:2010-03-27 Online:2010-12-05 Published:2010-12-05

Abstract:

Oxiracetam is often used as a nootropic agent. In this study, the NMR characteristics and conformation of oxiracetam were investigated. It was shown that the protons on the sidechain methylene group are magnetic nonequivalent because of the anisotropy effect of pyrrolidine ring. H6 and H3 showed long-range coupling, due to the partial double-bond character of the amide bond on the pyrrolidine ring. Pyrrolidine ring favored envelope conformation. Hindered internal rotation of another amide bond on the side chain was also analyzed.

Key words: NMR, conformation, 2D NMR, VT NMR, Oxiracetam, long-range coupling

CLC Number: