DIAMINES. 
§ 688 .] 
523 
§ 688. Ethylidenediamine. —Brieger found in putrid haddock, in the filtrate from 
the mercury chloride precipitate :—gadinine, neuridine, a base isomeric with ethy- 
lenediamine C 2 H 8 N 2 (but which Brieger subsequently more or less satisfactorily 
identified with ethylidenediamine), muscarine, and triethylamine ; these bases were 
separated as follows :— 
The filtrate from the mercury chloride solution was freed from mercury by SH 2 , 
evaporated to a syrup, and then extracted with alcohol. From the alcoholic solu¬ 
tion platinum chloride precipitated neuridine ; this was filtered off, the filtrate freed 
from alcohol and platinum, and the aqueous solution concentrated to a small volume 
and precipitated with an aqueous solution of platinum chloride ; this precipitated 
ethylidene platinum chloride. The mother liquor from this precipitate was concen¬ 
trated on the water-bath, and, on cooling, the platinochloride of muscarine crystal¬ 
lised out. From the mother liquor (freed from the crystals), on standing in a 
desiccator, the gadinine double salt crystallised out, and from the mother liquor 
(freed from gadinine after removal of the platinum by SH 2 ) distillation with KHO 
recovered trimethylamine. 
From the platinochloride of ethylenediamine, the chloride can be obtained by 
treating with SH 2 , filtering, and evaporating; by distilling the chloride with a 
caustic alkali, the free base can be obtained by distillation. 
Ethylidenediamine is isomeric with ethylenediamine, but differs from it in the 
following properties:—Ethylidenediamine is poisonous, ethylenediamine is non- 
poisonous. 
Ethylenediamine forms a platinochloride almost insoluble in hot water, while the 
ethylidene salt is more easily soluble. The properties of the gold salts are similar, 
ethylenediamine forming a difficultly soluble gold salt, ethylidene a rather soluble 
gold salt. 
Ethylidenediamine forms a hydrochloride, C 2 H 8 N 2 2HC1, crystallising in long 
glistening needles, insoluble in absolute alcohol, rather soluble in water. The 
hydrochloride gives precipitates in aqueous solution with phospho-molybdic acid, 
phospho-antimonic acid, and potassium bismuth iodide ; the latter is in the form of 
red plates. 
The platinochloride, C 2 H 8 N 2 2HCl.PtCl (Pt=53-6 per cent.), is in the form of 
yellow plates, not very soluble in cold water. 
Ethylidenediamine, when subcutaneously injected into guinea-pigs, 
produces an abundant secretion from the mucous membranes of the 
nose, mouth, and eyes. The pupils dilate, and the eyeballs project. 
There is acute dyspnoea ; death takes place after some twenty-four 
hours, and the heart is stopped in diastole. 
Trimethylenediamine is believed to have been isolated by Brieger 
from cultivations in beef broth of the comma bacillus. 
It occurs in small quantity in the mercuric chloride precipitate, and 
is isolated by decomposing the precipitate with SH 2 , evaporating the 
filtrate from the mercury sulphide to dryness, taking up the residue 
with absolute alcohol, and precipitating by an alcoholic solution of 
sodium picrate. The precipitate contains the picrate of trimethylene¬ 
diamine, mixed with the picrates of cadaverine and creatine. Cada- 
verine picrate is insoluble in boiling absolute alcohol, the other picrates 
soluble ; so the mixed picrates are boiled with absolute alcohol, and the 
insoluble cadaverine filtered off. Next, the picrates of creatinine and 
trimethylenediamine are freed from alcohol, the solution in water 
acidified with hydrochloric acid, the picric acid shaken out by treatment 
with ether, and then the solution precipitated with platinum chloride ; 
