Hydrolytic Changes in Solutions of Stilbamidine

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Abstract
Summary and Conclusions: The formation of 4—carbamyl—4′—amidinostilbene and 4:4′—dicarbamylstilbene from solutions of stilbamidine had been shown to occur when the latter were maintained for a number of weeks at 37°C., in diffuse light, and to a lesser extent when kept at the same temperature completely in the dark. When the same solutions were maintained at temperatures which varied from 5° to 20 °C. the formation of amides did not take place. Henry’s observations made in the Sudan have been confirmed. Good yields of the amides were obtained by autoclaving solutions of the parent substance at 1 to 2 atmospheres pressure for several hours. The monoamide was inactive against T. rhodesiense or T. congolense infections of mice and does not appear to be selectively absorbed by the trypanosomes like the active stilbamidine. The fact that solutions of stilbamidine autoclaved under the conditions employed by Oastler and Fidler undergo no demonstrable change and are not more toxic for mice than similar solutions freshly prepared, suggests that the lesions encountered by these authors in dogs were due to unchanged stilbamidine.
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