Abstract
In order to determine the structure of the new compound, having excellent hemostatic activity, tentatively designated as AC-44, the sulfonic acid compound (A), C9H13O5NS, prepared from epinephrine and sodium hydrogen sulfite, was studied. Methylation of (A) with dimethyl sulfate and sodium hydroxide afforded a nitrogenfree sulfonic acid (B), C10H12O3S, with generation of trimethylamine. Ozonic oxidation of (B) gave veratric acid and reaction of (B) with potassium cyanide gave 3, 4-dimethoxycinnamic acid via its nitrile. Therefore, (B) is 2-(3, 4-dimethoxyphenyl)ethanesulfonic acid and (A) would be 1-methylamino-2-(3, 4-dimethoxyphenyl)ethanesulfonic acid. These are all new reactions. These results have established the structure of AC-44 as sodium 1-methyl-5-semicarbazono-6-oxo-2, 3, 5, 6-tetrahydroindole-2-sulfonate.
