Amines Related to Epinephrine. I. Some Amines of the “Eprocaine” Type¹

Abstract

A solution containing 4.78 g. (5 ml.) of glycol in 100 ml. of water was refluxed for 5.75 hours. The characteristic odor of methyl isopropyl ketone became evident within one hour. A 25-ml. sample of the solution required 0.45 ml. of 0.141 N sodium hydroxide to neutralize the acid produced. Analysts for ketone indicated a yield of 1.2%. In another experiment where 1.2 g. of sodium carbonate was added at first, no ketone was formed.Refluxing and stirring 16.63 g. (10 ml.) of trimethylethylene bromide with 200 ml. of water and 10 g. of sodium carbonate for six hours gave no detectable amount of ketone. The dibromide phase, however, disappeared in two hours.

Beta-Phenethylamine Derivatives

“…This compound possesses the structure of both the procaine anesthetic type and the pressor arrangement under consideration here; consequently it is described as a pressor anesthetic. It is regrettable that the pressor activity is described in such indefinite terms (51,72). Furthermore, should eprocaine prove to produce an appreciable rise in blood pressure, it will be surprising; for this will mean that the virtual substitution of a procaine residue on the amino nitrogen will be active in contrast to other molecules having large substituents attached to the nitrogen atom.…”