Some derivatives of gelsemine / by Charles W. Moore.

  • Moore, Charles Watson.
Date:
1911
Catalogue details

Licence: In copyright

Credit: Some derivatives of gelsemine / by Charles W. Moore. 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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    0'3490,t made up to 20 c.c. with chloroform, gave +0°50' in a 2-dcm. tube, whence [a]i, +23’9°. Acetylgelsemine hydrochloride, C2oH2i'ON2’OAc,HCl, was pre- pared by passing dry hydrogen chloride into an ethereal solution of the base. It crystallises readily, in small prisms, from a mixture of methyl alcohol and ethyl acetate: 0-1346 gave 0’0510 AgCl. Cl = 9-3. C22H2403N2)HC1 requires Cl = 8-8 per cent. Gehemine Methiodide, C2„H2202N2,CH3l.—This substance was first prepared by Goeldner (Zoc. cit.), but it was not correctly characterised by him. It crystallises from alcohol in large, hand- some prisms, and from water in glistening leaflets containing one molecule of water of crystallisation : 0‘6006,* when heated at 120°, lost 0‘0210 H2^- H20 = 3'5. 0-1632 t gave 0-3250 CO2 and 0 0790 H2O. C = 54-3; H = 5-4. 0-2820 t » 0-1420 Agl. 1 = 27-2. C2]H2502N2l)H20 requires H20 = 3 7 per cent. C21H25O2N2I requires C= 54-3; H=5-4; 1 = 27 4 per cent. 0-2050,t made up to 20 c.c. with water, gave -f0°11' in a 2-dcm. tube, whence [a]p -1-8-9°. With the object of obtaining the corresponding gelsemethine, a quantity (1 gram) of gelsemine methiodide was heated at 200° for some hours with abo-ut 25 c.c. of 20 per cent, aqueous potassium hydroxide. When cool, the alkaline liquid was acidified, filtered, rendered alkaline with sodium carbonate, and extra.cted with ether. A quantity of a substance was thus removed, which, after crystal- lisation from acetone, formed glistening prisms, melting at 178°, and was found to be gelsemine. It is thus seen that gelsemine methiodide behaves in an anoma- lous manner on heating with potassium hydroxide, inasmuch as it does not yield the expected gelsemethine, but is deprived of methyl alcohol, the original base being regenerated. For the preparation of gelsemine methyl hydroxide, the corre- sponding methiodide was treated with silver sulphate, and to the resulting methosulphate the requisite amount of barium hydroxide was added. After removing the barium sulphate, the strongly alkaline aqueous solution of the quaternary hydroxide was concen- trated to the consistency of a syrup, but all attempts to isolate the methyl hydroxide in a crystalline condition were unsuccessful. On heating an aqueous solution of gelsemine methyl hydroxide at 220—240°, the base was found to undergo a change analogous to that shown above to occur when the corresponding methiodide