AMINES DERIVED FROM PROTEIN n 



Methylamine, Ethylamine, Dimethylamine. 



Methylamine occurs according to Trier [1912, 3; p. 8] in species of 

 Mercurialis and the root of Acorus Calamus and has been frequently 

 met with as a product of bacterial action (see P. Rona, Biochemisches 

 Handlexicon, Band IV, p. 80 1). It is perhaps formed from glycine, by 

 decarboxylation, but so far it has not been possible to demonstrate this 

 experimentally. The source of methylamine is in most cases more 

 probably trimethylamine (from choline). Thus Hasebroek [1887] 

 obtained this amine along with ammonia by the anaerobic putrefaction 

 of choline, and Morner [1896] found amines present in a peculiar 

 Swedish food (" surfisk "). This fish is pickled with a little salt and 

 allowed to ferment anasrobically ; it probably contains monomethyl- 

 amine, and certainly dimethylamine and choline, but not putrescine or 

 cadaverine. Ackermann and Schutze [1910, 1911] also found that a 

 little methylamine, together with trimethylamine, is formed by the action 

 of Bacterium prodigiosum on choline. Emmerling [1897] obtained 

 mono- and trimethylamine by the action of Streptococci on fibrin, but 

 here also the amines appear to be derived from admixed lecithin. 



Ethylamine was said more than fifty years ago to be produced in 

 the putrefaction of yeast and of wheat flour, but these observations re- 

 quire confirmation. It might result by the decarboxylation of alanine, 

 from which it is indeed formed on destructive distillation. 



Dimethylamine was stated by Bocklisch [1885] and by Morner 

 [1896] to occur in putrid fish, and by Ehrenberg [1887] in cultures 

 from a bacillus isolated from poisonous sausages. In the latter case 

 at least a confusion with putrescine was not unlikely, since the platini- 

 chlorides of the two bases have nearly the same composition. If 

 dimethylamine is formed at all it would be most probably derived from 

 choline and trimethylamine, although it could also result from the 

 decarboxylation of sarcosine (from creatine). 



Trimethylamine, N(CH 3 ) 3 . 



Trimethylamine occurs in the leaves of Chenopodium Vulvaria (the 

 Stinking Goosefoot) where it is readily detected by the odour on bruis- 

 ing the leaves ; it is also present in hawthorn flowers (Cratcegus 

 Oxyacanthd] and in ergot. Unlike the other amines dealt with in 

 this chapter, trimethylamine is not formed from an amino-acid, but is 

 a decomposition product of choline and allied quaternary bases ; it is 

 therefore of common occurrence in putrefaction. Thus it is present in 

 herring brine, the first natural source to be discovered by Winckler in 



