The constituents of the bulb of Buphane disticha / by Frank Tutin.

  • Tutin, Frank.
Date:
1911
Catalogue details

Licence: In copyright

Credit: The constituents of the bulb of Buphane disticha / by Frank Tutin. 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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    Buphanitine Methiodide, C23H2406N2,CH3I.-This derivative was quickly formed on adding methyl iodide to an alcoholic solution of the base. It crystallised readily from slightly diluted alcohol^ in slender, glistening prisms, which melted and decomposed at 278 . 0 1582 gave 0'2944 C02 and 0'0740 H20. C = 50’7; H = 5'2. C23H24OgN2,CH3I requires C = 50'9; H = 4’8 per cent. The alkaline aqueous liquid from which the buphanitine had been removed by means of chloroform was found to contain no acid, but only a very small amount of brown resin. It is thus evident that buphanine is not an ester of buphanitine, and it would appear probable that the latter is formed by the addition of one or more molecules of water to the former. Isolation of Narcissine, C1(5H1704N. The amyl-alcoholic solution of the bases which were not removed by extraction with ether, as previously described, was evaporated to a low bulk, freed from a small amount of amorphous, non-basic material, and the filtered liquid poured into a large volume of ether. The clear mixture was then washed with water, when a relatively small amount of an alkaloid was removed. This base could not be crystallised, nor could any crystalline salt be obtained from it. The ether-amyl alcoholic liquid was then kept for some time, when a small amount of narcissine separated (m. p. 267°. Found, C = 67'l; H = 6 0. Calc., C = 66'9; H = 5'9 per cent.). A direct comparison of this base with a specimen of narcissine obtained from the bulb of the common daffodil, kindly supplied by Mr. A. J. Ewins (compare Trans., 1910, 97, 2406), confirmed the identity of the two. Narcissine picrate, ClfiH]704N,CtiH307N3, has not previously been described. It crystallises readily in bright yellow plates, which decompose and melt at 196—199°. The liquid from which the narcissine had separated was frac- tionally extracted with hydrochloric acid in a manner similar to that already described, when it was resolved into two products of varying affinity for acid, but the weakly basic material was very small in amount. The first four fractions obtained by shaking with dilute hydrochloric acid were alkaline, and, on keeping, deposited some narcissine, which was removed. The filtrates from this base then yielded small amounts of narcissine hydrochloride, but the greater part of the material contained in them was amorphous, and consisted chiefly of buphanine, since it gave buphanitine on hydrolysis.