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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    was isolated, which differed from cpogelsemine by its Insolubility in hot water. This substance crystallises from dilute alcohol or ethyl acetate in glistening prisms. It begins to decompose at about 220°, but shows no deffnite melting point: 0T304 gave 0-3230 COg and O'OSOO HgO. C = 67'5j H = 6-8. 0-1382 „ 0-3416 OOg „ 0-0836 HgO. 0 = 67 4; H = 6-7. 02485 „ 17-0 c.c. Ng at 25° and 782 mm. N = 7-8. 0-2782 „ 0-1070 AgCl. Cl = 9-5. ^20^23^2^2^^ requires C=67 0; H = 64; N = 7-8; 01=9 9 per cent. This substance would thus appear to be a monochloro-derivative of apogelsemine, more particularly as it can be obtained by boiling apogelsemine -with hydrochloric acid. On hydrolysis it does not, however, regenerate opogelsemine, but yields a crystalline isomeride of the latter. It would therefore appear probable that the chloro- derivative is not related directly to apogelsemine, but to the new crystalline isomeride. It is therefore proposed to designate it as chloroiaoa.pogelsemine, its hydrolytic product being named isoapo- gelseminc. A determination of its specific rotatory power gave the following result: 0 2448, made up to 20 c.c. with chloroform, gave +1°49' in a 2-dcm. tube, whence [a]p +74 2°. Chloroisoa,pogelsemine A urichloride, C2oH2a02N2Cl,HAuCl„H20. ■—This salt crystallises from dilute alcohol in orange prisms, which decompose at 160°, and appear to retain a molecule of water which is not lost at 120°: 0-1820 gave 0-0494 Au. Au = 27’l. C2oH2402N2ClgAu,H20 requires Au = 27-5 per cent. Chloroiao&pogelsemine Methiodide, ^20^23^2^2^^>^^3^* This substance was prepared by the action of methyl iodide on an alcoholic solution of chloroisoapogelsemine. It crystallises from methyl alcohol in glistening prisms, melting and decomposing at about 265°: 0-1485 gave 0 2750 CO2 and 0-0740 H2O. C = 50-5; H=5 5. ^21^26^2^2^^^ requires C = 50-3; H = 5-2 per cent. Chloroar.etyliao&pogelsemine, C2oH220N2Cl'OAc. — Chloroisoapo- gelsemine was dissolved in about ten times its weight of acetic anhydride, and, after the addition of a drop of pyridine, the solution was boiled for two hours. The reaction mixture was then poured into water, the base precipitated by means of sodium carbonate, and extracted with chloroform. Ghloroacetyliao&pogelsemine crystal-