284 SCIENCE PROGRESS 



When either codeine methiodide or codeine methohydroxide 

 is treated with hot caustic soda solution a tertiary base is 

 obtained which Hesse has named methylmorphimethine : 



c ™>(C,.H„0).N<™ : 



[Morphine is not quite analogous to codeine or piperidine 

 in that the methohydroxide — 



HO / CH -. 



HO >(C 16 H 14 0) : N^CH, 



is very stable towards alkalis, and does not yield the expected 

 morphimethine when heated with strong soda. This is due, 

 Vongerichten 1 suggests, to the probable formation of a com- 

 paratively stable phenolbetaine. 



HCX /CH, "I 



>(C 16 H l4 0) : N/-CH 3 



By the action of hydrochloric acid or acetic anhydride, methyl- 

 morphimethine can be decomposed, as Knorr 2 has shown, 

 into hydroxyethyldimethylamine and a nitrogen-free body 

 which is a derivative of phenanthrene and is identical with 

 Vongerichten's methylmorphol. 



HO\ /CH 3 HO\ /CH S 



>(C, 6 H 13 0) . N( = >C„H 8 + HO.CH..CH,,.N< 



CH3O/ \CH 3 CH3O/ \CH 3 



Methylmorphimethine Methylmorphol Hydroxyethyldimethylamine 



When acetic anhydride is used in the above reaction, there is 

 formed a considerable proportion of a body isomeric with methyl- 

 morphimethine, ^-methylmorphimethine \ which by exhaustive 

 methylation yields the methyl ether of morphenol, a non- 

 nitrogenous substance differing from morphol by two atoms 

 of hydrogen. 



1 Ber. 30, 354- 



J Ibid. 22, 181, 1 1 13 ; 27, 1114. 



