THE BROMINE AND lODINE COMPOUNDS OF 

 HEXAMETHYLENETETRAMINE 



• ICANEMATSU SUGIURA and K. GEORGE FALK 

 (Harriman Research Laboratory, Roosevelt Hospital, New York City) 



(Received for publication, November i6, 1915) 



The extensive therapeutic use of hexamethylenetetramine (uro- 

 tropin, cystogen, formin, etc.), made a simple quantitative method 

 for its estimation desirable. A study of the Compounds which it 

 forms with bromine and iodine showed that such a method may be 

 based upon the formation of the tetraiodide. 



The nitrogen content of a number of preparations of hexameth- 

 ylenetetramine on the market was determined by the Kjeldahl 

 method and found to be very close to the calculated value for a 

 substance of the formula (CH2)6N4. 



Bromine derivatives. Legier^ described a dibromine deriv- 

 ative and Horton^ both a di- and a tetrabromine derivative. When 

 bromine and finel}'- powdered hexamethylenetetramine were allowed 

 to stand under a bell jar or in a desiccator, in separate vessels, bro- 

 mine was taken up as described by Horton; but, contrary to his 

 results, a product of a definite composition could not be obtained 

 in this way. The number of bromine atoms taken up varied with 

 the length of time the reaction was allowed to proceed and the 

 amount of washing, with ether, of the resulting product. Nitrogen 

 determinations showed that, after long continued action as many as 

 five atoms of bromine were taken up per molecule of hexameth- 

 ylenetetramine. Under the microscope it was evident that mixtures 

 were present, consisting of yellow dibromine derivative and red Com- 

 pounds containing a greater proportion of bromine. Similar mix- 

 tures were obtained in the reaction between aqueous solutions of 

 hexamethylenetetramine and bromine water. The preparation and 



1 Legier: Ber., 18, 3350 (1885). 



2 Horton: Ber., 21, 1999 (1888). 



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