528 POISONS I THEIR EFFECTS AND DETECTION. [§§ 694 697 . 
Both these diamines are poisonous. Metaphenylenediamine pro¬ 
duces, in the dog, the symptoms of an aggravated influenza 
with continual sneezing and hoarse cough, which, if the dose 
is large enough, ends in coma and death. Paraphenylenediamine 
produces exophthalmia, the tissues of the eye undergoing complete 
alteration. 1 
Both compounds, in doses of 100 mgr ms, per kilo., cause more or 
less salivation, with diarrhoea. The para-compound is more poisonous 
than the meta-compound. So far, neither of these diamines has 
been separated with certainty from the urine of sick persons, nor from 
products of decomposition. 
§ 694. Hexamethylenediamine, C 6 H 10 N 2 . — Hexamethylenediamme 
has been found by A. Garcia 2 in a putrefying mixture of horse-flesh 
and pancreas. 
§ 695. Diethylenediamine, C 4 H 10 N 2 , is a crystalline substance, 
melting-point 104°, boiling-point 145°-146°. After melting, it solidifies 
on cooling, forming a hard crystalline mass. It is extremely soluble in 
water, and is deposited from alcohol in large transparent crystals. A 
technical product called “ spermin piperazidin ” or “ piperazine has 
been found by A. W. v. Hoflmann 3 to be identical with diethylene¬ 
diamine. The hydrochloride crystallises in colourless needles, insoluble 
in alcohol, readily soluble in water. The platinochloride, C 4 H 10 N 2 H 2 
PtCl 6 , is in smail yellow needles, and is fairly easily soluble in hot 
water, but dissolves but slightly in hot alcohol. The mercuro-chloride, 
C 4 H 10 N 2 H 2 HgCl 4 , crystallises in concentrically grouped needles, and is 
readily soluble in hot water, but is reprecipitated on adding alcohol. 
The picrate, C 4 H 10 N 2 ,C 6 H 2 (NO 2 ) 3 OH, crystallises from water in yellow 
needles, almost insoluble in alcohol . 4 
§ 696. Mydaleine is a poisonous base discovered by Brieger in 
putrid animal matters. It is probably a diamine, but has not been 
obtained in sufficient quantity for accurate chemical study. The 
platinochloride is extremely soluble in water, and only comes down 
from an absolute alcohol solution. It has been obtained in a crystal¬ 
line form, giving on analysis 38 - 74 per cent, of platinum, C 10 83 per 
cent., H 3-23 per cent. 
Mydaleine is very poisonous. Small quantities injected into guinea- 
pigs cause dilatation of the pupil, an abundant secretion from the nose 
and eyes, and a rise of temperature. Fifty mgrms. cause death. The 
post-mortem appearances are not distinctive ; the heart is arrested in 
diastole ; the intestines and bladder are contracted. In cats it causes 
profuse diarrhoea and vomiting. 
§ 697. Guanidine. —Guanidine may be considered to have a relation 
1 Compt. Rend., cvii. 533-535. 
3 Ber., xxiii. 3297-3303. 
2 Zeit. f. physiol. Chem., xvii. 543—555. 
4 Sieber, J., Ber., xxiii. 326-327. 
