252 BACTERIAL POISONS. 



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

 the choline double salt (Haenack). 



Physiological Action. — Small doses of this ptomaine 

 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 

 atropinized frogs. Very small doses produce in rabbits 

 profuse salivation and lachrymation, 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. 



t 



Constitution of the Members of the Choline 

 Group. — The structure of choline was clearly demon- 

 strated by WuRTZ, who accomplished the synthesis of this 

 base by treatment of ethylene chlorhydrine wnth trimethyl- 

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

 of betaine and neurine by using monochloracetic acid and 

 vinylbromide instead of ethylene chlorhydrine. The struc- 

 tural formulse which can be deduced from these reactions 

 are as follows : 



CH,OH CH^ CO,H CIipH 



CH, CH Cir CHOH 



I I I I 



N(CH3)3.0H N(CH3)3.0H N(CH3)3.0H NCCHj^.OH 



Choline. Neurine. Betaine. Muscarine, 



The formulas 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 : 



CH3 



I 

 CH, 



I 

 N(CI-l3)3.0II. 



