The constitution of epinephrine / by H.A.D. Jowett.

  • Jowett, H. A. D. (Hooper Albert Dickinson)
Date:
[1904]
Catalogue details

Licence: In copyright

Credit: The constitution of epinephrine / by H.A.D. Jowett. Source: Wellcome Collection.

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    The determination of the specific rotation of the base in dilute acetic acid solution gave the following result : aD = -10'; Z=0-25 dcm. ; c = 2*084; [a]D= -32-0°. Pauly (loc. cit.) found [a]D —43°, but considering the small observed angle (10') the above figures do not vary beyond the limits of experimental error. The general statements of previous observers as to the solubility of epinephrine in various solvents and its behaviour towards alkaloidal reagents were confirmed. The base did not react with phenyl- hydrazine. Oxidation with Permanganate. Five grams of epinephrine were dissolved in dilute sulphuric acid and oxidised at the ordinary temperature with a 1 per cent, solution of permanganate, 30 grams of this reagent being required to produce a permanent colour. The product yielded methylamine, which was identified by its platinichloride. 0T646 gave 0*0688 Pb. Pt = 41*8. (CH5N)2,H2PtCl6 requires Pt = 41*3 per cent. The acids obtained were formic and oxalic acids. Fusion with Potassium Hydroxide. Five grams of epinephrine were added to 25 grams of potassium hydroxide and the mass fused at as low a temperature as possible. The melt was then dissolved in water, acidified, and extracted with ether. The residue, after distilling off the ether, was obtained crystal¬ line and gave the characteristic protocatechuic acid reaction on adding successively ferric chloride and sodium carbonate. The amount ob¬ tained was insufficient to admit of further examination. Methylation and Subsequent Oxidation with Permanganate. Four grams of epinephrine were dissolved in 50 c.c. of methyl alcohol in which 1 gram of sodium had been dissolved, and 8 grams of methyl iodide added. The mixture was then heated in a sealed tube at 100° for four hours, the alcohol distilled off, and the operation repeated with the residue. After the second methylation, the residue was dissolved in water and then added to an aqueous solution of 17 grams of silver nitrate, the silver iodide quickly filtered off, and the filtrate saturated with hydrogen sulphide and again filtered. The filtrate was then oxidised with a 2 per cent, solution of perman-