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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    12.-J2 hydroxide with water, at about 200“, an anomalous change takes place, inasmuch as the expected gelsemethine is not formed, gelsemine being regenerated with the elimination of methyl alcohol. The methyl hydroxide of apogelsemine behaves in an analogous manner, as on heating with water opogelsemine is regenerated. Experimental. The gelsemine employed was isolated from the dried rhizome and roots of Gelsemium sempervirens, Aiton, in the manner previously described (loc. cit.). The alkaloid crystallises from acetone in handsome, glistening prisms, melting at 178®, and has [a]p +15'9° in chloroform solution. As already mentioned, it possesses the empirical formula ConHgoOoNo. It is monobasic, and its hydrochloride, CaoHgjOjNo.HCl, forms small, glistening prisms, melting at about 300°, and having [a]jj +2'6° in aqueous solution. Gelsemine is not attacked by even prolonged heating with potassium hydroxide solution or by treatment with sodium in boiling alcoholic solution. On the other hand, it is very readily oxidised by potassium permanganate, but no definite products have been obtained by this means. The alkaloid contains no methoxyl or ethoxyl group. Acetylgelsemine, C2oH2jON2*OAc.—The presence of a hydroxyl group in gelsemine has already been shown by Goeldner Qoc. cit.), who obtained the acetyl and benzoyl derivatives of the base in the form of their hydrochlorides. The acetylated base, however, has not previously been described. A quantity (5 grams) of gelsemine was boiled for one hour with acetic anhydride (50 grams) in the presence of a trace of pyridine. The reaction mixture was then shaken with ice and water until a homogeneous liquid was obtained, after which the base was precipi- tated by sodium carbonate and extracted with ether. Acetylgelsemine crystallises from methyl alcohol in large, colour- less prisms, containing one molecule of the solvent, which melt indefinitely at 60—70°. The methyl alcohol of crystallisation is partly lost by exposure to the air, and completely on heating at 100°, after which the base melts at 106—108°: 0 3760,* when heated at 100°, lost 0 0295 CII^O. CH40 = 7 8. 0T256 t gave0'3333 CO2 and 0'0760 H2O. C = 72'4; H = 6‘7. 0 1304 1 ,, 0-3460 CO2 „ 0 0778 HoO. C = 72'3; H = 6'7. C22H2403N2,CH40 requires €£[40 = 8'1 per cent. C22H24O3N2 requires C=72'5; H = 6'6 per cent. * Air-dried. t Dried at 120°.