16 THE SIMPLER NATURAL BASES 



Emmenthaler cheese (Winterstein and Thony [1902]). Van Slyke 

 and Hart [1903] found a little putrescine in ordinary Cheddar 

 cheese, but none in a sterile chloroform cheese. 



According to Garcia [1892-3, 2, 3] the yield of the diamines from 

 putrid horse meat and from pancreas is diminished by the addition of 

 carbohydrates (compare p. 25); four-fifths is already formed in the 

 first twenty-four hours of incubation and the maximum is reached 

 after three days. Once formed, putrescine and cadaverine appear to be 

 very resistant to bacterial action. Gulewitsch [ 1 894] obtained cadaverine 

 from horse meat kept four months at 1 5. 



Hyoscyamus muticus contains tetramethyl-putrescine (see appendix). 



Agmatine, C 5 H U N 4 . 



Agmatine, or guanidino-butylamine, was obtained by Kossel 

 [1910, i] from herring spawn after heating with dilute sulphuric acid 

 (5 per cent, by volume) in an autoclave at 4 atmospheres pressure. 

 The base differs from arginine by CO 2 , the chief amino-acid in herring 

 spawn, so that it may be considered as being derived from arginine by 

 decarboxylation : 



NH. 2 . C( : NH) . NH . CH 2 . CH 2 . CH 2 . CH 2 . NH 2 agmatine. 

 NH 2 . C( : NH) . NH . CH 2 . CH 2 . CH 2 . CH(NH 2 ) . COOH arginine. 



Agmatine has also been isolated from ergot by Engeland and Kutscher 

 [1910, I, 2] who obtained from their base on oxidation guanidine and 

 guanidino-butyric acid, 



NH 2 . C( : NH) . NH . CH 2 . CH 2 . CH a . COOH. 



Kossel [1910, 2] synthesised agmatine from cyanamide and tetra- 

 methylene diamine, 



NH 2 . CN + NH 2 (CH.) 4 NH 2 = NH 2 . C(:NH). NH . (CH,) 4 . NH 2 . 



Phenyl-ethylamine, C 6 H 5 . CH 2 . CH 2 . NH 2 . 



/3-Phenyl-ethylamine is of some interest, since it was the first putre- 

 faction base of which the composition was determined. Nencki 

 [1876] obtained the base from a mixture of 200 grams of ox pancreas 

 and 600 grams of gelatin dissolved in 10 litres of water, which was 

 putrefied at 40 for five days. 



Nencki, like Selmi and other early investigators of putrefaction 

 bases, was most impressed by their analogy to vegetable alkaloids such 

 as coniine and nicotine, and he at first considered his base to be a pyri- 

 dine homologue, dimethylpyridine or collidine. Finding later that his 

 hydrochloride, unlike that of collidine, yielded on destructive distilla- 



