RECENT WORK ON THE MORPHINE GROUP 297 



iodide only. The above formulae may therefore be amplified 

 as follows : 



HO\ CH 3 0\ CH,O v 



>(C 16 H u O):N.CH 3 ; >(C„H l4 0): N.CH,; >(C 16 H l2 0) : N. CH 3 



ho/ ho/ ch 3 o/ 



Morphine Codeine Thebaine 



The existing knowledge of the thebaine molecule is largely 

 due to the work of Freund, 1 who has subjected the base to a 

 series of decompositions similar to those carried out with 

 morphine and codeine. By heating with acetic anhydride, 

 thebaine is resolved into methylhydroxyethylamine and the 

 acetyl derivative of a nitrogen-free compound which, by analogy 

 with morphol, has been named thebaol : 



CH 3 O v CHaO. 



>(C, 6 H ls O) : N.CH 3 + 2(CH 3 CO),0 = >(C I4 H 7 )O.COCH 3 + CH 3 COOH + 



CH s O' CH 3 



Thebaine Acetylthebaol 



CH 3 CO. 



+ >N.CH,.CH,.O.COCH, 



CH/ 



Diacetylmethylhydroxyethylamine 



Similarly, by treating thebaine methiodide with acetic anhydride 

 in the presence of silver acetate, acetylthebaol and the acetyl 

 derivative of dimethylhydroxyethylamine are obtained : 



CH 3 0\ CH 3 0\ 



>(C ls H,.,0) : N(CH 3 ),I + (CH 3 CO).,0 = >(C. 4 H 7 )0 . COCH 3 + HI + 



CH3O/ CH 3 0/ 



Thebaine methiodide Acetylthebaol 



CH 3 X 



+ >N .CH a .CHo. O .COCH 3 



CH 3 / 



Acetyldimethylhydroxyethylamine 



These reactions are entirely analogous to the decomposition 

 of methylmorphimethine into acetylmethylmorphol and di- 

 methylhydroxyethylamine. 



Constitution of Thebaol 



By distillation with zinc dust, thebaol is converted into 

 phenanthrene, and, as it can readily be demonstrated that 

 thebaol contains two methoxy groups and one phenolic 



1 Ber. 30, 1364. 



