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XVII. — Studies on the Pharmacological Action of Tetra-Alkyl-Ammonium 

 Compounds. By Professor 0. R. Marshall. 



(Head December 15, 1913. MS. received July 17, 1914. Issued separately February 26, 1915.) 



III. THE ACTION OF METHYL-ETHYL-AMMONIUM CHLORIDES. 



In view of the differences observed in the pharmacological action of tetra- 

 methyl- and tetra-ethyl-ammonium chlorides, it seemed of interest to investigate 

 the actions of the methyl-ethyl-ammonium compounds. The chlorides of these 

 compounds — namely, tri-methyl-ethyl-ammonium chloride, di-methyl-di-ethyl- 

 ammonium chloride, methyl-tri-ethyl-ammonium chloride — were kindly prepared 

 for me by Dr J. E. Mackenzie, who has published the mode of preparation and 

 the analysis of them.* 



The only references I. have found to the pharmacological action of the members 

 of this series are brief statements by Tappeiner t and Boehm4 Tappeiner says that 

 tri-ethyl-methyl-ammonium chloride, unlike tetra-methyl-ammonium chloride, does 

 not produce temporary paralysis of the respiration ; Boehm that tri-methyl-ethyl- 

 ammonium chloride, like tetra-methyl-ammonium chloride, causes contracture of 

 an isolated frog's muscle when a solution is applied to it. In a later communication 

 Boehm § gives a table of the concentration limits of certain substances which just 

 fail to produce a maximal paralysis of the myo-neural junction. In this the follow- 

 ing percentages are given to members of the series included in the present investi- 

 gation : tetra-methyl-ammonium chloride, '005 per cent. ; tri-methyl-ethyl-ammonium 

 chloride, "015 per cent. ; tetra-ethyl-ammonium chloride, "125 per cent. 



The solutions used in the investigation were mainly isotonic solutions and 

 solutions of the same electrical conductivity, or these diluted with 0'6 per cent, 

 sodium chloride or Ringer's solution. Owing to the hygroscopic nature of the 

 substances the strength of the solutions was determined by estimating the amount 



Substance. 



Percentage 

 Found. 



Percentage 

 Calculated. 



Sodium chloride ..... 

 Tetra-methyl-ammonium chloride 

 Tri-methyl-ethyl ammonium chloride 

 Di-methyl-di-ethyl ammonium chloride 

 Methyl-tri-ethyl-ammonium chloride . 

 Tetra-ethyl-ammonium chloride 



0-895 

 1-76 



2-20 

 253 

 301 

 3-45 



1-68 



1-90 

 211 

 2-33 

 2-54 



of chloride by Volhardt's method. The table above shows the strengths of 



* Jonrn.f. prakt. Chem., lxxxiv. p. 549 [1911]. I desire to express my thanks to Dr Mackenzie for this service. 



t Arch.f. exp. Path. u. Pharmak, xxxvii. p. 349 [1896]. 



I Ibid., lviii. p. 267 [1908]. § Ibid., lxiii. p. 224 [1910]. 



TRANS. ROY. SOC. EDIN., VOL. L. PART II. (NO. 17). 69 



