RECENT WORK ON THE MORPHINE GROUP 301 



When energetically reduced, 1 thebenol yields the hydrocarbon 

 pyrene which, according to Bamberger and Philip, 2 possesses 

 the configuration : 



In the formation of morphothebaine, the oxygen ring of 

 thebaine is opened, thus giving rise to a hydroxyl group : 



CH Ov CH s O\ 



^ 3 ^)(C l6 H l2 0) : N . CH 3 -> HO-J(C„H„) : N . CH 3 



CHsCK HO/ 



Thebaine Morphothebaine 



The second hydroxyl is, of course, produced by the decom- 

 position of a methoxyl group. 



Apomorphine 



As previously mentioned (p. 281), apomorphine is produced 

 by the action of dehydrating agents upon morphine : 



C, 7 H 19 3 N - H 2 = C l7 H 17 2 N 



Dankwortt 3 succeeded in preparing a monoacetyl derivative 

 of apomorphine, whence he concluded that only one of its two 

 oxygen atoms was present as a hydroxyl group, while the 

 other was combined in the same manner as the " ether-like " 

 oxygen in morphine. Recently, however, Pschorr, Jaeckel, 

 and Fecht* have proved that both ot the oxygen atoms in 

 apomorphine are present as hydroxyl groups. Dimethylapo- 

 morphine combines with only one molecule of methyl iodide, 

 so that the nitrogen in apomorphine is tertiary. One of the 



1 Ber. 30, 1383. 3 Annalen, 228, 572. 



2 Annalen, 240, 147. 4 Ber. 35, 4377. 



