ナルセイン

ナルセイン 化学特性,用途語,生産方法

• 解説

  ナルセイン．アヘン中に0.1～0.5％ 含有されるアルカロイド．単離が困難なので，(±)-ナルコチンより合成される．融点145 ℃(無水和物)，176 ℃(水和物)．pKa 9.3，pKb 10.7(20 ℃)．熱エタノールに易溶，酸性あるいはアルカリ性の水に可溶．エチルエステル(エチルナルセイン)塩酸塩は麻酔作用をもち，鎮痛，鎮咳薬として用いられる．

• 説明

  An alkaloid of opium (Papaver somniferum) was first isolated by Pelletier in 1832 but not characterized until some years later by Couerbe and Anderson, the latter assigning to it the formula C23H2909N which was accepted until Freund showed that it contains H20 of crystallization. The base remains in the mother liquors after removal of the major alkaloids. It forms slender, colourless needles or prisms of the trihydrate, m.p. 170°C. It is optically inactive and dissolves readily in alkalies forming metallic derivatives. It behaves as a weak, monoacidic base forming well-crystallized salts. The hydrochloride crystallizes with 5.5 H20 from cold, dilute HCI, or as the trihydrate from hot solutions. From MeOH it yields crystals with 1 mole of solvent, m.p. 190-2°C. The aurichloride forms reddish-yellow needles, m.p. 130°C and the picrate has m.p. 195°C. With chlorine water, followed by the addition of ammonia, it gives a characteristic blood-red colour while with dilute iodine solution, the solid alkaloid develops a blue colour. With ethyl nitrite, narceine forms an oximino derivative which, on exhaustive methylation, furnishes trimethylamine, hemipinic acid and 2-cyano-3- methoxy-4: s-methylenedioxy-1-vinylbenzene.

• 純化方法

  Recrystallise Narcein from water (as trihydrate). The styphnate has m 185-189o (from EtOH), and the picrate has m 200o (from EtOH). [Beilstein 19 H 370, 19 I 797, 19 II 386, 19 IV 4382.]

• 参考文献

  Couerbe., Annalen, 17,171 (1836)
  Anderson., ibid, 86, 182 (1853)
  Roser., ibid, 247, 167 (1888)
  Freund, Frankforter., ibid, 277,20 (1893)
  Freund, Oppenheimer., Ber., 42, 1084 (1909)

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