The constitution of epinephrine / by H.A.D. Jowett.
- Jowett, Hooper Albert Dickinson, 1870-1936.
- Date:
- [1904]
Licence: Attribution 4.0 International (CC BY 4.0)
Credit: The constitution of epinephrine / by H.A.D. Jowett. Source: Wellcome Collection.
Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.
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![C10H15OoN, and showed that, although it acted as a mono-acidic base, it gave no reaction with the usual alkaloidal reagents. Aldrich, however, preferred the slightly different formula C9H1303N. Abel, who carefully purified his material, adopted the formula C10H13O3’N’,^HoO, but adduced absolutely no evidence to show that it contained any water of crystallisation. His results agree equally well with Aldrich’s formula C9H]303lSr. This is seen from the following numbers calculated for each formula : (Aldrich’s formula) C9H1303H requires O = 59'0; H = 7T ; N = 7'6. (Abel’s formula) C10H13O3N,JH2O requires C = 58-8 ; H = 6-9 ; N = 6'9. Abel actually found C = 58-4 to 58'7 ; H = 6'8to7'2; H = 7-l to 7'6 per cent. Von Fiirth (Monatsh., 1903, 24, 261) confirmed the formula C9H]303N by analyses and molecular weight determinations. Pauly (Ber., 1903, 36, 2945), from the results of the analysis of very carefully purified material, also confirmed this formula, so that it must be considered the most probable of those proposed. Ho crystalline salts or derivatives have been described, but von Fiirth prepared a tribenzoyl- and a tribenzenesulpho-derivative. He also showed that it contained no methoxyl group, and that it yielded methylamine by treatment with concentrated acids. Of the degradation products of epinephrine, only protocatechuic acid, formed by fusion with potassium hydroxide, has been posi- tively identified, although substances giving the pyrrole, skatole, or catechol reactions have been obtained by different observers. Von Fiirth suggested for the base the partially developed formula [CH3*NC2H,OH]C6H6(OH)2, and Pauly, who determined its specific rotation, suggested that it contained a hydroxylated benzene residue attached to one of five possible complexes, of which the most probable were the following : •CH-OH -CH-NH-CHg ch2-hh-ch3 and CH2-OH In this way, the formation of catechol, skatole, or pyrrole deriva- tives would be easily explained. In the present investigation, I have confirmed the formula C9H1303N, first proposed by Aldrich, by analyses of carefully purified material and by molecular weight determinations. By fusion with potassium hydroxide, a small quantity of a crystalline substance giving the reactions of protocatechuic acid was isolated, but the amount was so small that it was doubtful whether the presence of this complex in the original substance could be correctly deduced from its formation.](https://iiif.wellcomecollection.org/image/b22401775_0006.jp2/full/800%2C/0/default.jpg)
