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Nuclear Magnetic Resonance Spectroscopic Studies on the Action of Ammonium Chloride to Chloroquine

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Abstract

In order to study the medically important action of ammonium chloride toward chloroquine or 7-chloro-4-(4′-diethylamino-1′-methylbutylamino)quinoline, the proton and carbon-13 nuclear magnetic resonance (NMR) spectra of chloroquine have been examined using a 400-MHz NMR spectrometer. Quinoline ring protons exhibited highly resolved coupling patterns of the first-order. The distortionless enhancement by polarization transfer (DEPT) spectra discriminated methyl, methylene and methine carbons in the diamino-chain where diamagnetic effects by nitrogen atoms are complicated. All assignments were fulfilled with carbon-proton correlation spetroscopy (COSY), besides homo-spin decoupling and DEPT spectra. The affinity of ammonium chloride with the chloro atom of the quinoline ring was observed in the proton NMR spectra. This fact seems to be related to the dose of ammonium chloride used to reduce the amount of chloroquine given to patients suffering from retinopathies.

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Authors and Affiliations

  1. Department of Synthetic Chemistry, Faculty of Engineering, Nagoya University, Nagoya, 464-01, Japan

    Yoshio Kosugi

  2. The 2nd Analytical Section, Shinnikka Kankyo Engineering, Co., Ltd., Sakinohama, Tobata, Kitakyushu, 804, Japan

    Tomoko Yamura

  3. Department of Applied Chemistry, Faculty of Engineering, Kumamoto University, Kumamoto, 860, Japan

    Yoshiaki Furuya

Authors
  1. Yoshio Kosugi
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  2. Tomoko Yamura
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  3. Yoshiaki Furuya
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Kosugi, Y., Yamura, T. & Furuya, Y. Nuclear Magnetic Resonance Spectroscopic Studies on the Action of Ammonium Chloride to Chloroquine. ANAL. SCI. 6, 165–169 (1990). https://doi.org/10.2116/analsci.6.165

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  • DOI: https://doi.org/10.2116/analsci.6.165

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