Researches on the constitution of physostigmine. Pt. 1 / by Arthur H. Salway.

  • Salway, Arthur H. (Arthur Henry)
Date:
[1912?]
Catalogue details

Licence: Public Domain Mark

Credit: Researches on the constitution of physostigmine. Pt. 1 / by Arthur H. Salway. Source: Wellcome Collection.

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    it was obtained in stellate clusters of colourless needles melting at 212°: 0*2772, heated at 110°, lost 0*0189 H20. H20 = 6*8. C13H190N2C1,H20 requires H20 = 6*6 per cent. 01071 gave0'2406 C02 and 0*0756 H20. 0=61*3; H = 7*8. 0*0983* „ 0*0564 AgCl. Cl=14*2. Ci3H19ON2C1 requires C = 61’3; II = 7*5; Cl = 14*0 per cent. Eseroline yicraie crystallises from alcohol in stellate clusters of yellow needles melting at 195° : Eseroline possesses feeble acidic properties, since it is readily soluble in alkali hydroxides, and can be recovered from the alkaline solution unchanged in the absence of air. It contains one methyl- imide group, NMe, the presence of which was proved by the method of Herzig and Meyer (Monatsh., 1895, 18, 379) : 0*1208 gave 0*0986 Agl. NMe=ll*4. C12H15ON(NMe) requires NMe = 13*3 per cent. In order to obtain if possible some knowledge of the state of combination of the oxygen atom of eseroline, the latter was treated with semicarbazide hydrochloride in dilute alcohol and the mixture kept for some time, but no reaction took place. Diazomethane in ethereal solution was likewise without action on eseroline. Acetic anhydride, on the other hand, appears to produce some change, but no definite product could be isolated from the reaction mixture. It would appear from these results that eseroline does not contain a carbonyl group, whilst the presence of a hydroxyl group is doubtful. Eseroline Methiodide.—When methyl iodide is added to a solution of eseroline in chloroform, reaction takes place with evolution of heat, and a crystalline precipitate immediately separates. This substance crystallises from water in thin, colourless needles melting at 196°: 0*1208 gave 0*2079 C02 and 0*0652 H20. C = 46*9; 11 = 6*0. C14H21ON2I requires C = 46*7; H = 5'8 per cent. It is evident that the above compound is formed by the combina¬ tion of one molecule of methyl iodide with one molecule of eseroline. The same compound is produced when an excess of methyl iodide is employed in the reaction; eseroline must therefore be a tertiary base. * The amount of chlorine in eseroline hydrochloride cannot be determined by simple precipitation with aqueous silver nitrate, since the latter is reduced by eseroline in the absence of nitric acid, whilst, in the presence of this acid, eseroline is decomposed with the formation of hydrocyanic acid, which forms, with, the silver nitrate, a precipitate of silver cyanide. The result recorded above was obtained by the Carius method.
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