318 POISONS : THEIR EFFECTS AND DETECTION. [§ 377. 
adult is about *1 grin. (1-5 grain) ; three times this quantity, -3 grin. 
(4-5 grains), would probably produce unpleasant, if not dangerous, 
symptoms. 1 
§ 377. Narceine, C 23 H 27 N0 8 4-3H 2 0.—Two of the three molecules of water are 
expelled at 100° ; the other molecule requires a higher temperature. Anhydrous 
narceine is hygroscopic, and melts in a tube at about 145° ; when exposed to air it 
unites with one molecule of water, and then melts at about 170°. 
The constitution of narceine, according to Freund and Frankforter, 2 may be 
represented thus :— 
ch 2 o 2 
ch 3 o 
/\ -COOH 
-OCH 3 
I 
och 3 
It therefore contains three methoxyl groups. 
Narceine forms good crystals, the form being that of long, four-sided rhombic 
prisms or fine bushy united needles. 
Narceine hydrochloride crystallises with 5|H 2 0 and with 3H 2 0 ; the anhydrous 
salt melts at 190°-192°. The platinochloride is a definite salt, m.p. 190°-191° ; it 
decomposes at 195°-196°. The nitrite forms good crystals, which decompose at 97°. 
Narceine also forms crystalline salts with potassium and sodium; these may be ob¬ 
tained by heating the base at 60°-70° with a 33 per cent, solution of NaHO or KHO. 
The potassium compound melts at 90°, the sodium at 159°-160°. The alkaloid is 
regenerated when the alkali salts are treated with acids or with C0 2 . Crude narceine 
may be purified by means of the sodium salt; the latter is dissolved in alcohol and 
precipitated with ether. 
It is soluble in alcohol, but almost insoluble in alcohol and ether, or benzene and 
ether, as well as in carbon tetrachloride ; it is slightly soluble in ether, carbon 
disulphide, and chloroform. It has no reaction on moist litmus-paper. 
Benzole and petroleum ether extract narceine neither from acid nor alkaline 
solutions ; chloroform extracts narceine both from acid and from alkaline solutions, 
the latter in small proportion only. Narceine turns the plane of polarisation to the 
left, a[r] —66-7°. Narceine may be separated from narcotine by the addition of 
ammonia to the acid aqueous solution ; narcotine is fully precipitated by ammonia, 
but narceine is left in solution. 
In the subliming cell it melts at 134°, but gives no crystalline sublimate. The 
tube melting-point of the trihydrate is 170°. The melted substance is at first colour¬ 
less ; but on raising the temperature, the usual transitions of colour through different 
shades of brown to black are observed. If melted, and kept a few degrees above its 
melting-point, and then cooled slowly, the residue is straw-coloured, divided into 
lobes, most of which contain feathery crystals. 
At high temperatures narceine develops a herring-like odour; the residue 
becomes darkish blue with iron chloride. Concentrated nitric acid dissolves it with 
1 For further details as to the action of codeine, the reader is referred to L. O. 
Wach’s monograph, Das Codein (1868), which contains reference to the earlier 
literature. See also Harley, The Old Vegetable Neurotics, London. 
2 M. Freund and G. B. Frankforter, Annalen, cclxxvii. 20-58. 
