BETAINES 49 



II I 



A 



CH 3 OH 



The isolation was carried out by means of potassium mercuric iodide, and conversion into 

 the gold and platinum salts. Kutscher and Lohmann [1906, 4 ; section on butyro-betaine] 

 obtained the same base from normal human urine (at first [1906, 3] they mistook it for 

 neurine). They [1907] consider that it is derived from the pyridine of tobacco smoke and 

 of roasted coffee; 10 litres of men's urine yielded 0*17 grm. of the aurichloride, and 100 

 litres of women's urine 2'6 grm. ; the greater content of women's urine they ascribe to 

 the " bekannte Vorliebe der Frauen fiir pyridinhaltigen Kaffee ". Roasted coffee beans con- 

 tain 0*02 per cent, of pyridine [Bertrand and Weisweiller, 1913]. Methyl-pyridinium 

 chloride has also been obtained from a commercial shrimp extract (Ackermann and Kutscher 

 [1907, 4 ; under betaine]). The physiological action was investigated by Kohlrausch [1909, 

 1911 ; under betaine]. The platinichloride (C 6 H 8 N) 2 PtCl 6 forms large orange coloured 

 plates, mp. 205-207, little soluble in cold water, readily in hot, and the aurichloride 

 C 6 H 8 NAuCl 4 yellow needles, mp. 252-253, very little soluble in cold water. 



Achelis and Kutscher [1907] obtained 0-7 grm. of 7-picoline aurichloride mp. 201 

 from 10 litres of horse urine. This salt has the same composition as the preceding and is 

 said to be derived from pyridine derivatives of the fodder. 



4. u O CO 



7-n-Butyro-betaine, (CH 3 ) 3 NSj >CH 2 



\CH 2 CH/ 



Among the ptomaines isolated by Brieger [1886, I, p. 27 ; Ch. I] 

 from horse meat which had putrefied for four months, was a base 

 C 7 H 17 O 2 N. The chemical and physiological properties, as described 

 by Brieger, correspond very closely with those of a betaine C 7 H 15 O 2 N 

 obtained a few years ago by Takeda [1910] from the urine of dogs 

 poisoned with phosphorus ; Engeland and Kutscher [1910, 3] obtained 

 Takeda's base by methylating 7-amino-butyric acid, so that there is no 

 doubt as to its constitution ; the identity with Brieger's base is almost 

 equally certain, in which case his formula should contain two hydrogen 

 atoms less. 1 



7-Butyro-betaine was first synthesised by Willstatter [1902, i ; under 

 betaine] and was also obtained by Krimberg [1907, 2] by the reduction 

 of carnitine (see next section). Brieger isolated it from that part of the 

 precipitate with mercuric chloride, which was the more soluble in water. 

 After removal of the mercury, the base was precipitated as aurichloride. 



The physiological action was studied in some detail by Brieger. 

 On frogs it has a curare action, in accordance with the fact that it is a 

 quaternary base and a 7-betaine. In the a-betaines so far described the 



1 Brieger's ptomaine and 7-butyro-betaine have a very similar composition, a gold salt of 

 identical melting point, a soluble picrate and similar reactions to alkaloidal reagents : both 

 arrest the frog's heart in diastole. 



4 



