252 BACTERIAL POISONS. 



in needles, and is difficultly soluble in water, more so than 

 the choline double salt (HARNACK). 



Physiological Action. Small doses of this ptoma'inc 

 induce in frogs total paralysis, with stoppage of the heart 

 in diastole, and this action is antagonized by subsequent 

 injection of atropine, as well as in the case of previously 

 atropinixed frogs. Very small doses produce in rabbits 

 profuse salivation and laehrymation, contraction of the 

 pupil, profuse diarrhoea, and passage of urine and semen; 

 finally, the animal dies in convulsions, which, however, are 

 only of short duration. 



CONSTITUTION OF THE MEMBERS OF THE CHOLINE 

 GROUP. The structure of choline was clearly demon- 

 strated by WURTX, who accomplished the synthesis of this 

 base by treatment of ethylene chlorhydrine with trimethyl- 

 amine. This same method can be applied to the synthe-is 

 of betaine and ueuriue by using monochloracetic acid and 

 vinylbromide instead of ethylene chlorhydrine. The struc- 

 tural formula? which can be deduced from these reactions 

 arc as follows : 



CILPH CII 2 CO 2 H CII 2 OH 



I II I I 



CH 2 CH OH, CHOII 



N(CH 3 ) 3 .OII N(CH 3 ) 3 .OH N(CH 3 ) 3 .OH N(CH 3 ) 3 .OH 



CIIOUNE. NEUBINE. BETAINE. MITSCARINK. 



The formula; of betaine and muscarine are ordinarily given 

 as the anhydrides, but there can be no doubt that the free 

 bases possess the structure indicated above. All these bases, 

 since they can be prepared from choline, may also be con- 

 sidered as oxidation-products of trimethyl-ethyl-ammonium 

 hydrate : 



CII 3 



CH 2 



N(CII 3 ) S .OII. 



