292 SCIENCE PROGRESS 



under these conditions methylmorphimethine is decomposed 

 with the formation of dimethylaminoethylether, the phenanthrol 

 ether proved itself completely stable even at a temperature of 

 150 . This characteristic difference in behaviour affords a proof 

 that the binding of the complex C 2 H 4 . N(CH 3 ) 2 in methylmor- 

 phimethine cannot be similar to that of the hydroxyethyldime- 

 thylamine in the synthetic body, and therefore cannot be attached 

 to the phenanthrene complex through the medium of the "indifferent" 

 oxygen. 



This conclusion is in agreement with the joint observation 

 of Knorr and Pschorr * that thebainone, when treated with acetic 

 anhydride, decomposes with the formation of hydroxyethyl- 

 dimethylamine in a manner similar to methylmorphimethine, 

 notwithstanding the fact that this ketone contains no " in- 

 different " oxygen. 



Thus, on the above grounds, the assumption of the presence 

 of an oxazine ring in morphine is untenable, and there is no 

 doubt that the " indifferent " oxygen atom must be regarded as 

 a member of a furane ring, as in the case of methylmorphenol, 

 the decomposition product of ^-methylmorphimethine, and as 

 forming a bridge between positions 4 and 5 of the phenanthrene 

 complex. The complex C 2 H 4 . N . CH 3 must therefore be united by 

 means of a carbon binding to the phenanthrene ring both in 

 methylmorphimethine and morphine. 



The Nitrogen Complex 



In order to obtain further information as to the manner in 

 which the basic portion of the decomposition products of 

 methylmorphimethine, codeinemethiodide, and thebainemeth- 

 iodide (see p. 297) are attached to the phenanthrene complex, 

 Knorr 2 has recently made a special study of these bodies. 

 When a-methylmorphimethine is decomposed with hydrochloric 

 acid gas, it yields methylmorphol and chloroethyldimethylamine 

 (see p. 284). As a matter of fact, the latter base is not actually 

 obtained, but, instead, a mixture of tetramethylethylenediamine, 

 (CH 3 ) 2 N . CH 2 . CH 2 . N . (CH 3 ) 2 , and hydroxyethyldimethylamine, 

 HO . CH 2 . CH 2 . N(CH 3 ) 2 . Knorr 3 has, however, found that a 

 mixture of the same bases is obtained when the salts of 



1 Ber. 38, 3172. * Ibid. 37, 3494. s Ibid. 3507. 



