Isolation, and Properties

Z-a-Narcotine was probably first observed by Derosne in 1804 (87), but its isolation may be attributed to Robiquet (88), who assigned to it the formula C23H26O7N. The accepted formula was first proposed by Mat-thiessen and Foster (89). The alkaloid opianine (90, 91) was shown by Hesse (92, 93) to be narcotine. A base regarded by Wertheim (94) as a homologue of narcotine has not been encountered again. 

Narcotine has been found only in opium or in the source plant, Papaver somniferum L., the content in opium being of the order of 0.7 to 6.4% (95-98), although some Persian opium may contain as much as 11.2 % (99), while a Chinese variety of P. somniferum is stated to be devoid of this alkaloid (100) as well as of papaverine. The seeds contain detectable amounts of the alkaloid, and the content in the dried plant is from 0.008 to 0.276 % (101) and depends upon the state of maturity of the plant. The reported presence of narcotine in a number of fruits and vegetables and its confusion with vitamin C are erroneous, or at best unconfirmed (102-106). 

The isolation of narcotine from opium is simplified by the fact that most of it remains in the water-insoluble residue when opium is processed for the manufacture of morphine. The narcotine is then extractable from this residue with dilute acids, and after regeneration from the extract it may be purified by recrystallization from ethanol (107). The acid oxalate, m.p. 174°, has also been used to separate it from its chief contaminant, namely, papaverine (92,108, 109). Its salt with camphorsulfonic acid is practically insoluble in water whereas that of the other opium salts are quite soluble (110). The free base may be quickly purified by passing a chloroform or benzene solution through a column of calcium hydroxide, most of the impurities being absorbed (HI). 

Narcotine is polymorphic (112, 113), being obtained in anhydrous stout needles when slowly crystallized from ethanol. It melts sharply 

The UV-absorption spectrum of narcotine has been frequently determined (150-153) and suggested as a quantitative method for its determination (151). Narcotine is fluorescent in ultraviolet light, the color of the emitted light depending upon the wave length of the incident light (154 157). 

Narcotine has been reported as present in Papaver rhoeas L. 33) and P. paeoniflorum Hort. 34). Some other sources are doubtful its occurrence in Rauwolfia heterophylla Roehm and Schult. 35) may be due to industrial impurities 36), and, for the same reason, the isolation of narcotine from Strychnos melinoniana Baillon is questionable 37). 

The recovery of narcotine from aqueous solution at varying pH values by ether extraction 38) and its solubility in a number of solvents 39) have been reported. The preparation of isotonic solutions has also been described 40). 

A number of salts of narcotine were prepared 41-50)—some for oral use, since they are less bitter 47-49). Regeneration from its picrate with an anion-exchange resin proceeds with an almost quantitative yield 41). Fluorescence of complexes of narcotine with manganese chloride and cadmium halides was studied 51, 52). 

Narcotine-N-oxide, a well-known compound 53), is of recent interest because of its possible use in medicine 22, 54-56). 

UV- and IR-spectra of narcotine have been reported 57-59) and used 

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