Dimethylamine Adducts of Barbiturates and Related Compounds and Their Application to Particle Size Reduction

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  • バルビツール酸誘導体, その関連化合物とジメチルアミン間の分子付加物の形成ならびにその微粉化への応用
  • バルビツールサン ユウドウタイ ソノ カンレン カゴウブツ ト ジメチルアミン

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Abstract

Adduct formation with dimethylamine was confirmed in 5 barbiturates (barbituric acid, mephobarbital, metharbital, phenobarbital, and propallylonal) and phenytoin. The thermal, physico-chemical, and micromeritical properties of these adducts were investigated by differential scanning calorimetry, thermogravimetry, thermomicroscopy, infrared spectroscopy, X-ray powder diffractometry, electron microscopy, and BET gas adsorption analysis. From thermogravimetry, the combining ratios of adducts (barbiturates or phenytoin : dimethylamine) were determined to be 1 : 1 for barbituric acid, mephobarbital, propallylonal, and phenytoin, and 1 : 2 for phenobarbital. As the new absorption band arising from NH2+ stretching vibration appeared in infrared spectra of almost all the adducts, it was strongly suggested that the bonding of an ionic nature would participate in the adduct formation. By desorption of dimethylamine from dimethylamine adducts under reduced pressure with or without heat application, effectively micronized original chemicals were recovered. Their specific surface areas were 2 to 3 times larger in comparison with the corresponding barbiturates recovered via ammonia adducts. The difference in effectiveness in particle size reduction would be attributable to the difference in molecular volume of dimethylamine from ammonia.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 102 (12), 1150-1161, 1982

    The Pharmaceutical Society of Japan

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