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Santoninum, active principle-an alkaloid -of Cina (Semen cinae)
COMMON NAME Santonin
As the authorities that I have consulted differ as to the name of this plant, let us, until we are shown our error, consider Cina as the Artemesia santonica, or European wormseed, and Santoninum as the Russian or Asiatic Artemesia pauciflora.
Obtained from different species of Russian and Levantine Artemisia, especially from "Semen cinae." See Cina.
Cina: Plantae; Spermatophyta, Angiospermae - Flowering Plants; Dicotyledonae; Asteridae / Synandrae; Asterales; Compositae / Asteraceae - Composites / Daisy or Sunflower Family
Allen: Cyclopaedia, V. 8, V. 10. Cyclop. Drug Path., V. 4. Macfarlan: High Pot. Provings.
Description of the substance
COMMON NAME, Santonin. A neutral principle prepared from Santonica (the unexpended flower heads of Artemisia maritima). It comes in colorless, shining, flattened crystals. Preparation.
History and Preparation.—Santonin, the vermifuge principle of santonica, was discovered, in 1830, by Kahler and Alms, simultaneously. The British Pharmacopoeia (1885) gives detailed directions for its preparation, which consists in boiling the bruised santonica seeds in water with addition of slaked lime, concentrating the solution of calcium santonate, adding hydrochloric acid, and allowing it to stand for 5 days. Wash the precipitated santonin (santonic anhydride) with water and ammonia water, which removes resin, and recrystallize from alcohol after treating the solution with animal charcoal. Another method consists in boiling out a mixture of santonica seeds and slaked lime with alcohol of 60 per cent (by volume), and decomposing the calcium santonate with carbonic acid (see Flückiger, Pharmacognosie des Pflanzenreichs, 3d ed., 1891, p. 822). (Also see detailed Bibliography on Santonin, by A. Van Zwaluwenburg, Pharm. Arch., 1899, pp. 1-11.)
Description.—Santonin occurs "in colorless, shining, flattened, prismatic crystals, odorless and nearly tasteless when first put in the mouth, but afterward developing a bitter taste; not altered by exposure to air, but turning yellow on exposure to light. Nearly insoluble in cold water; soluble in 40 parts of alcohol at 15° C. (59° F.), in 250 parts of boiling water, and in 8 parts of boiling alcohol; also soluble in 140 parts of ether, in 4 parts of chloroform, and in solutions of caustic alkalies. When heated to 170° C. (338° F.), santonin melts, and forms, if rapidly cooled, an amorphous mass, which instantly crystallizes oil coming in contact with a minute quantity of one of its solvents. At a higher temperature, it sublimes partly unchanged, and, when ignited, it is consumed, leaving no residue. Santonin is neutral to litmus paper moistened with alcohol. Santonin yields, with an alcoholic solution of potassium hydrate, a bright pinkish-red liquid, which gradually becomes colorless. From its solution in caustic alkalies, santonin is completely precipitated by supersaturation with an acid"—(U. S. P.).
Santonin (C15H18O3) is the anhydride of santonic acid (C15H20O4), which is a derivative of dimethyl-naphtalene (C10H6[CH3]2). Santonin dissolves in alkalies with formation of salts of this acid. Santonin, in acetic acid solution, when exposed to sunlight for about a month, is converted into (colorless) photosantonic acid (C15H22O5). The ethyl-ester of the latter is obtained when an alcoholic solution of santonin is exposed to sunlight (Sestini). The yellow coloration developed upon exposure of santonin to light, is believed to be due to a red resin. Santonin is optically laevo-rotatory
Adulterations and Tests.—Santonin has been adulterated by boric acid; this substance may be recognized by being insoluble in chloroform, or by not being volatilized when heated on platinum foil. If the residue is dissolved in water, and the solution acidulated with hydrochloric acid, a strip of yellow turmeric paper is colored brown by it. Santonin, turned yellow from exposure to light, has been mistaken for picric acid; the latter is easy of detection, being soluble in cold and hot water with yellow color (J. M. Maisch, Amer. Jour. Pharm., 1874, p. 52); or the white crystals of santonin might be mistaken for strychnine, the latter, however, may readily be distinguished by the violet coloration it produces with sulphuric acid and potassium dichromate (see Strychnina). Other substitutions, e. g., salicin, may be recognized by the following U. S. P. directions for santonin: "Its solution in cold, concentrated sulphuric acid is at first colorless (absence of easily carbonizable, organic substances), but, after some time, turns yellow, then red, and finally brown. If water be added, immediately after it is dissolved without color in sulphuric acid, it will be completely precipitated, and the supernatant liquid should not have a bitter taste, nor should it be altered upon the addition of potassium dichromate T.S. (absence of brucine or strychnine), or of mercuric potassium iodide T.S. (absence of alkaloids in general)"—(U. S. P.). D. Lindo's test for santonin is as follows: Dissolve, in a test-tube, a small quantity of santonin in strong sulphuric acid, add a few drops of a highlydiluted solution of ferric chloride; upon warming in the flame of a Bunsen burner, a beautiful violet coloration is developed.