210 BACTERIAL POISONS. 



oil, soluble in water, from which it can be extracted with 

 ether. This oil, on treatment witli phenol and sulphuric 

 acid, gives LIEBERMANN'S nitroso-reaction, which would 

 seem to show that putrescine is not a primary diamine 

 (butylenediamine), but is rather a secondary diamine 

 (BRIEGER, II., 42). As a primary diamine it should take 

 up, on repeated treatment with methyl iodide, six methyl 

 radicals ; whereas, if it is a secondary diamine, only four 

 methyl radicals can enter the molecule. Thus, to illustrate, 

 methylamine, CII 3 .NH 2 (a primary amine), combines with 

 three molecules of methyl iodide to form (CH 3 ) 4 N.EII. 

 Similarly, dimethylamine (CH 3 ) 2 .NH, requires only two 

 molecules to form (CH 3 ) 4 N.HI. In the case of diamines, 

 double this number of methyl groups is required to effect 

 complete saturation. As a matter of fact, BRIEGER (III , 

 101), on treating putrescine with methyl iodide, has suc- 

 ceeded in introducing four, and only four, methyl radicals. 

 From this, however, it does not follow that putrescine is 

 not a primary amine, since cadaverine, an unquestioned 

 primary diamine, yields a substitution compound contain- 

 ing only two methyl groups (see p. 215). 



The tetra-methyl substitution-product of putrescine, 

 C 4 H 8 (CH 3 ) 4 N 2 , can be distilled without decomposition. The 

 free base crystallizes in long prisms. The hydrochloride 

 forms small needles which are easily soluble ; with phos- 

 photungstic acid it gives a white crystalline precipitate, 

 with phosphomolybdic acid a yellow crystalline precipitate, 

 with picric acid needles. Potassium-bismuth iodide gives 

 a brownish-red amorphous deposit, while the potassium 

 mercuric iodide forms prisms. Gold chloride yields diffi- 

 cultly, and platinum chloride easily soluble octahedra ; 

 aqueous mercuric chloride forms needles. 



The aurochloride has the formula C 8 H 22 N 2 .2AuCl 4 . 



This tetra-methyl derivative of putrescine is enormously 

 poisonous as compared with putrescine. The symptoms 

 are the same as those produced by muscarine or neurine. 

 They are: abundant salivation; dyspnoea respiration at 

 first increases, then decreases ; contraction of the pupils ; 

 paralysis of the muscles of the limbs and trunk ; increased 



