466  '    Conversion  of  Morphia  into  Codeia.  {^"sept"' 
Jour.  Pharm. 
1881. 
THE  CONVERSION  OF  MORPHIA  INTO  CODEIA. 
By  E.  Grimaux. 
The  formula  of  morpliia,  Cj^H^gNOg,  and  that  of  codeia,  CigHgiNOg, 
show  that  these  two  bases  differ  from  each  other  by  CH^,  and  that 
codeia  can  be  considered  as  a  devivative  from  morphia  by  the  substi- 
tution of  a  CH3  group  for  one  atom  of  hydrogen.  In  1853,  How/ an 
English  chemist,  tried  the  action  of  iodide  of  methyl  upon  morphia 
and  codeia ;  but  he  obtained  an  isomer  of  hydriodate  of  codeine, 
not  presenting  any  characters  of  an  alkaloidal  salt,  not  precipitated  by 
ammonia  or  potash,  and  behaving  like  a  quarternary  iodide  of  am- 
monium. 
More  recently,  Matthiessen  and  Wright  have  defined  the  relation 
between  morphia  and  codeia.  By  heating  morphia  with  hydrochloric 
■acid  they  removed  from  it  the  elements  of  water  and  converted  it  into 
■apomorphia ;  codeia,  submitted  to  the  same  treatment,  yielded  also 
apomorphia  and  besides  chloride  of  methyl.  They  have  therefore 
admitted  the  existence  in  morphia  of  an  alcoholic  group  (HO)  and 
in  codeia  that  of  a  group  (OCH3) ;  but  nothing  indicated  the  possibil- 
ity of  the  passage  from  one  base  to  the  other. 
In  considering  the  various  reactions  of  morphia,  its  reducing  prop- 
erties, its  solubility  in  potash,  lime  water  and  baryta  water,  and  the 
coloration  that  it  takes  with  ferric  salts,  I  thought  that  it  approached 
the  phenols  in  its  characters.  Morphia  might  be  a  body  having  com- 
plex functions,  containing  at  least  one  phenolic  hydroxyl,  and  codeia 
would  then  be  the  methylic  ether  of  morphia  considered  as  a  phenol. 
In  order  to  attempt  this  conversion  it  only  remained  to  apply  the 
knoNvn  process  of  heating  morphia  with  alcoholic  potash  or  soda  and 
iodide  of  methyl. 
Upon  taking  1  mol.  of  morphia,  dissolved  in  alcohol  containing  1 
mol.  of  soda,  adding  2  mol.  of  iodide  of  methyl  and  heating  the  mix- 
ture gently,  a  brisk  reaction  was  observed,  which  terminated  in  a  few 
moments.  The  phenomenon  occurred  as  expected,  but  it  was  compli- 
cated by  a  secondary  reaction.  Instead  of  free  codeia,  iodo-methylate 
of  codeia,  CH3l,C\7Hi8N02(OCH3),  was  obtained  to  the  extent  of  85 
per  cent,  of  the  theoretical  yield.  At  the  same  time  there  was  a 
double  decomposition  between  the  iodide  of  methyl  and  the  morphia- 
soda,  another  part  of  the  iodide  of  methyl  being  fixed  directly  upon 
the  molecule. 
