12 THE SIMPLER NATURAL BASES 



1855. On an industrial scale it is formed by the destructive distilla- 

 tion of beet sugar molasses ; here the parent substance is betaine. 



Examples of the production of trimethylamine by pure cultures 

 are the action of Proteus vulgaris on wheat gluten and on meat, of 

 Bacillus liquefaciens on commercial gelatin and of Bacteriumprodigiosum 

 on choline and on lecithin. Ackermann and Schutze [1910, 1911] 

 found that the last-named organism does not produce trimethylamine 

 from betaine, and that B. vulgatus does not decompose choline. 



The alleged occurrence of trimethylamine in urine has been the 

 subject of several investigations. Long ago Dessaignes [1856] ob- 

 tained it by distillation of urine with caustic soda (37 grm. of the free 

 base from 65 litres of human urine). He, however, left open the 

 question whether trimethylamine is present as such or is formed by the 

 decomposition of some other compound by the alkali. This question 

 was likewise left unanswered by de Filippi [1906] who worked out 

 a process for the estimation of urinary trimethylamine (see appendix). 



Takeda [1909] used magnesium oxide instead of caustic soda, 

 and distilled under reduced pressure ; he found no trimethylamine in 

 the urine of horses and of dogs and only doubtful traces in human 

 urine ; it is however formed in putrefaction. Kinoshita [1910, l], using 

 Herzig and Meyer's method for the estimation of N-methyl groups, 

 found only traces, and Erdmann [1910] has also arrived at the con- 

 clusion that " fresh normal urine does not contain trimethylamine ". 

 According to Kutscher the trimethylamine in urine is formed from 

 such bases as novaine and reducto-novaine. 



Isobutylamine, 3 cH . CH 2 . NH 



This base was obtained by the putrefaction of racemic a-amino- 

 isovaleric acid (d.l. valine) by Neuberg and Karczag [1909]. A 

 solution of 10 grams of the amino-acid in 450 c.c. of water, with a 

 little KC1, Na 2 HPO 4 and MgSO 4 was rendered alkaline with sodium 

 carbonate and yielded after inoculation and four weeks' incubation at 

 37 0-424 grm. of a platinichloride (C 4 H n N) 2 H 2 PtCl 6 , mp. 226-227, 

 in all probability that of isobutylamine. 



A butylamine has also been obtained by Gautier from cod liver oil 

 prepared by the old putrefactive process. 



In Fagara xanthoxyloides isobutylamine occurs in combination with 

 piperonylacrylic acid as an amide, fagaramide (Thorns and Thumen, 



Isobutylamine is the lowest amine causing any appreciable rise of 

 blood pressure when injected intravenously. 



