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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    The quantity of material available did not suffice for its further examination. \soa\ioGehemine, It has already been stated that, on crystallising the mixed hydro- chlorides obtained by the action of hydrochloric acid on gelsemine, only about 80 per cent, of the product was readily obtained in a crystalline condition. ■ The material contained in the filtrate from the crystalline hydrochlorides was therefore dissolved in water, excess of sodium carbonate added, and the base extracted with a large volume of chloroform. On concentrating the chloroform solution, a substance separated from the boiling liquid in small, colourless prisms, melting at about 290—300°. This compound was found to be identical with that obtained by the hydrolysis of chloroisoopogelsemine, and has been designated as isoapopeZsemme. After recrystallisation from alcohol, the melting point became constant at about 310°: 0T390 gave 0-3614 COj and 0 0920 HgO. C = 70-9; H=7-3. 0-1408 „ 0-3641 CO2 „ 0-0920 H2O. C = 70-5; H = 7-2. 0-2432 „ 17-0 c.c. N, at 26° and 764 mm. N = 7'8. C20H24O3N2 requires C = 70 6; H = 7-lj N = 8'2 per cent. 0-4812, made up to 20 c.c. with pyridine, gave Oj, +0°48' in a 2-dcm. tube, whence [a]j, +16’6°. isoapoGelsemine is almost insoluble in most solvents, with the exception of pyridine, in which it dissolves fairly readily. isosu^oGehemine Hydrochloride, C2oH2403N2,HCl,H20.—This salt was prepared in the same manner as apogelsemine hydrochloride. Like the latter, it retains one molecule of water of crystallisation, which is not lost on heating at 120°: 0-1200 gave 0-2656 CO2 and 0-0788 H2O. 0 = 60 4; H = 7-3. C2(jH2.r,03N2Cl,H20 requires C = 60-8; H = 6 '8 per cent. 0 2090, made up to 20 c.c. with water, gave +0°34' in a 2-dcm. tube, whence [0]^, -t-27-l°. isoapoGefsemirae Methiodide, C2oH2403N2,CH3l.—This substance was formed by the action of methyl iodide on zsoapogelsemine in alcoholic solution. It crystallises from methyl alcohol in glistening plates, melting and decomposing at 266°: 0-2445 gave 0-1180 Agl. I = 26‘0. ^21^27^3^2^ requires 1 = 26-3 percent. A determination of its specific rotatory power gave the following result: 0 3260, made up to 20 c.c. with water, gave Oj, -1- 0°55' in a 2-dcm. tube, whence [a]j, -(-28-1°.