CI 15511

Description

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.

Definition

ChEBI: Narceine is a stilbenoid.

Purification Methods

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.]

References

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)