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Keywords:

  • Soterenol—fluorometric analysis after trihydroxyindole reaction, pharmaceutical formulations;
  • Mesuprine—fluorometric analysis after trihydroxyindole reaction, pharmaceutical formulations;
  • Trihydroxyindole reaction—with methanesulfonanilides, fluorometric analysis of soterenol and mesuprine;
  • Methanesulfonanilides—trihydroxyindole reaction applied, fluorometric analysis of soterenol and mesuprine;
  • Adrenergic agents—soterenol and mesuprine, fluorometric analysis, pharmaceutical formulations

Abstract

Methanesulfonanilides, like soterenol and mesuprine, which are bioisosteric with adrenergic catecholamines, form fluorescent species when subjected to the trihydroxyindole reaction. Presumably, the fluorescence is due to adrenolutin-like species formed from aminochrome intermediates. Fluorescence was not induced in a relative of soterenol where a methyl group was added to the sulfonamido nitrogen, a fact that suggests the presence of a quinoid intermediate in the reaction scheme of soterenol. A ring isomer of soterenol, where the methanesulfonamido and hydroxyl groups were interchanged, produced only about 5% as much fluorescence response as soterenol. The soterenol counterparts to isoproterenol and isoproterenolsulfonic acid did not produce fluorescence when treated like soterenol. This finding and the fact that response was linear with concentration for soterenol and mesuprine suggest that a fluorometric analysis could be developed for these methanesulfonanilides.