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)
ナルセイン 上流と下流の製品情報
原材料
準備製品