Some Reactions of Ammonolyzed Epinephrine

Abstract

Previous work1 on certain nitrogenous substances in liquid ammonia has shown that some of them tend to ammonolyze with changes in their physical, chemical, and biological properties. Ammonolyzed edestin was reported2 not to have given an anaphylactic reaction with a guinea pig previously sensitized to the untreated edestin. Recent observations on changes in some physical constants of certain amino acids in liquid ammonia indicate an ammonolysis. Epstein, Gunn and Virden3 have shown changes brought about in the physiological activity of phenylethylamines by methylation. These facts, in addition to the observations of Kraus and White4 that the hydroxyl groups of alcohols and phenols are quite reactive in liquid ammonia and to the report of Roberts and Miller5 that the phenolic group of tyrosine seems to be acidic in liquid ammonia have led us to believe that epinephrine could be ammonolyzed and thus altered in its physiological activity.The chemical treatment consisted of adding 60 mg. of Parke, Davis adren...