Narcissine : an alkaloid from the bulb of the common daffodil (Narcissus pseudonarcissus) / by Arthur James Ewins.

  • Ewins, Arthur James.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Narcissine : an alkaloid from the bulb of the common daffodil (Narcissus pseudonarcissus) / by Arthur James Ewins. 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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    .brown, flocculent precipitate. This polyphenolic substance, again, could be extracted by ether from its acid solution, but on evaporating off the solvent only a very small quantity of a brown, amorphous product was obtained, and all attempts to obtain a crystalline product were fruitless. On account of the relatively large number of oxygen atoms present in the molecule, it was thought possible that a carboxyl group might be present, but attempted esterification showed the absence of such grouping. For this reason and from the absence of methoxy-groups as shown by the Zeisel reaction, the formation of a polyphenolic derivative such as has been described is very possibly due to the presence in the molecule of a methylenedioxy-grouping and a phenolic bridge oxygen. The stability of the alkaloid would seem to support such a view, although there is, of course, no direct evidence of such structure. Experiments with regard to the physiological action of the alkaloid were carried out in these laboratories by Dr. P. P. Laidlaw, to whom I am indebted for the following account of its action. As tested on frogs and cats, the alkaloid showed no action in any way similar to that of pilocarpine or of atropine. 0T25 Gram, given by mouth to a cat, caused nausea, vomiting, salivation, and purgation. The salivation was not, however, similar to that produced by pilocarpine, since it could not be produced on the anaesthetised animal. Experimental. Preparation of the Alkaloid. Two thousand five hundred bulbs of the common daffodil (Narcissus pseudonarcissus), weighing approximately 4 kilos., were dried at a temperature of about 40°. The weight of the dried product was 1400 grams. The substance was finely ground and extracted for about six hours with hot alcohol (97 per cent.), and the alcoholic extract evaporated to about 200 c.c. To the dark syrupy, acid liquid was added an equal volume of water, and a very dark resinous precipitate which formed was collected. This precipitate was re-suspended in a little very dilute acid, and again collected after thoroughly shaking. The filtrate and washings were combined, and the acid liquid extracted twice with about one-third of its volume of ether. The aqueous solution was then rendered alkaline by addition of sodium carbonate, when, after some time, a precipitate formed, which consisted mainly of bunched prisms. The crystals were collected, and after recrystallisation from 90 per cent, alcohol were obtained as colourless, short, stout prisms, melting at 266—267° (bath at 250° at commencement of heating). The sub- stance was dried first in air, then in a vacuum over sulphuric acid,