RECENT WORK ON THE MORPHINE GROUP 291 



The hydroxyl group in position 6 undoubtedly corresponds 

 to the alcoholic hydroxyl group of morphine, since the other is 

 in the ortho position to the methoxyl group occupying posi- 

 tion 3, and cannot therefore be alcoholic. Moreover, as will 

 be seen later, the hydroxyl group in position 6 forms part ol 

 a ring which in morphine is in a reduced condition, and would 

 therefore be expected to exhibit alcoholic properties. 



By a process of elimination, the hydroxyl group in position 4 

 must correspond to the " indifferent " oxygen of morphine and 

 morphenol. 



The nature of the " indifferent" oxygen atom and the point 

 of attachment of the nitrogen-containing side chain to the 

 phenanthrene complex are closely bound up with one another. 

 At one time Knorr thought that the oxygen formed a bridge 

 between the two groups, especially as morphine in many of its 

 properties closely resembled a base morpholine (q.v.) which 



O 



contains the grouping H 2 C CH 2 . On this assumption methyl- 

 morphimethine would be represented by the formula 



,OCH 3 



O . CH, . CH, . N 



'CH 3 

 \CH 3 



H a 



OH 



a structure of the same type as that ot the phenanthrol ethers, 1 

 prepared by the interaction of the sodium salt of methyl morphol 

 and chlorethyldimethylamine, 



OCH 3 



O. CH,.CH, .N 



/CH 

 X \CH 3 



Knorr has compared the behaviour of these two bodies when 

 treated with a solution of sodium ethoxide, and finds that whilst 



1 Ber. 38, 3172. 



