joo SCIENCE PROGRESS 



These facts show that the group 



I 

 o=c 



in codeinone corresponds to the group 



I 

 CH 3 0— c 



\ 



in thebaine. Codeinone is a ketone derived from codeine by 

 the oxidation of its alcoholic hydroxyl group, thus : 

 CH 3 cn CH 3 cn 



HCi,H, 4 0) : N . CH 3 + O = HC 16 H I ,0) : N . CH 3 + H 2 



HOJ 0:J 



Codeine Codeinone 



It follows that thebaine is the methyl ether of the enolic form 

 of codeinone and, by analogy with morphine, probably possesses 

 one of the two following formulae : 



H H 



CH 3 



CH3O 



CH 3 



CH 3 



Thebenine is a secondary base, and when subjected to 

 ■exhaustive methylation yields trimethylamine and a nitrogen- 

 free substance named thebenol \ the latter is very stable towards 

 alkali, for even on fusion only the methyl group is split off and 

 .another substance, nor-thebenol, 1 obtained : 



CH 3 

 CH 3 



(C 16 H,,0) : N . CH 3 



Thebaine 



CH 3 

 HO 



CH a O 



HO' 



>(C 16 H 10 O) 



Thebenol 



1 Ber. 30, 1382. 



^(C l6 H 11 0).NHCH 3 



Thebenine 



HO\ 



>(C 16 H l0 O) 

 HO/ 



Non-thebenol 



