The constitution and synthesis of damascenine, the alkaloid of Nigella damascena / by Arthur James Ewins.

  • Ewins, Arthur James.
Date:
1912
Catalogue details

Licence: In copyright

Credit: The constitution and synthesis of damascenine, the alkaloid of Nigella damascena / 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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    LXIl.—The Constitution and Synthesis of Damascenine, the Alkaloid of iVigella damascena. By Arthur James Ewins. The alkaloid damascenine was first isolated by Schneider (Pharm. Centr.-h., 1890, 31, 173) from the seeds of Nigella damascena. He described it as a crystalline solid melting at 27°, and assigned to it the composition C10Hi5O3N. This work is now shown to be substan- tially correct, the composition of the alkaloid being actually repre- sented by the formula C10H]3ORN, differing only from the former in having two hydrogen atoms less. Until now, however, the work of Schneider has been obscured by the results of Pommerehne, who assigned to the alkaloid the formula C9Hn03N (Arch. Pharm., 1900, 238, 531), and stated that it was readily converted by alkalis into an isomeric acid, damasceninic acid. This formula was, moreover, accepted by Keller (Arch. Pharm., 1904, 242, 299), who later (ibid., 1908, 246, 1) obtained an alkaloid from Nigella aristata having the composition C]0H13O3N, which he termed “ methyldamascenine.” As will be shown later, however, this is the only alkaloid present in J igella, and is identical with Schneider’s damascenine. The constitution of damasceninic acid, which is readily formed from damascenine, was, however, fairly conclusively shown by Keller to be 2-methylamino-3-methoxybenzoic acid (1), the synthesis of which he unsuccessfully attempted. From this acid “ methyl- damascenine ” (III) was obtainable, but in order to explain the supposed isomerism of the acid with damascenine a betaine-like