168 
Researches  on  the  Cinchona  Alkaloids. 
/  Am.  Jour.  Pliarm. 
(       April,  1881. 
From  the  group  X,  which  is  still  unknown  in  its  parts,  there  would 
sometimes  be  formed  ethylpyridin  and  acetic  acid,  and  sometimes  oxalic 
acid  and  ammonia,  according  to  the  method  of  action.  By  the  trans- 
formation of  quinia  into  chitenin  the  methoxyl  remains  perfectly  intact, 
while  the  CHg  group,  on  the  contrary  is  eliminated. 
€H,  =  CJiJ^,  I  g^H'  +  40  =  C,,H„N A  {  oS"'  +  CH A 
In  a  similar  manner  cinchotenin  is  formed  from  cinchonia,  and  cin- 
chotenidin  from  homocinchonidia. 
Using  chromic  acid  as  the  oxidizing  agent,  the  group  X  is  appa- 
rently destroyed ;  CHg  is  transformed  into  COOH ;  on  the  one  hand 
quinic  acid  (oxymethylchinolincarbonic  acid)  COOH.CyH^N.OCHg, 
and  on  the  other  hand  chinolincarbonic  acid  are  produced. 
We  have  seen  that  quinia,  cinchonidia,  and  their  isomers,  by  the 
treatment  with  hydrochloric  aeid  suffer  a  molecular  change,  and  that 
at  the  .same  time,  in  the  case  of  quinia  and  quinidia,  methyl  is  elimi- 
nated : 
C«H^N,  I  g{j^='+HCl=CH,Cl+C,,H,<,N,.(OH),. 
The  new  bases  manifested  themselves  generally  as  unsaturated  com- 
pounds, in  that  each  took  up  one  molecule  of  hydrochloric  acid. 
Whether  now  this  addition  took  place  on  the  group  X  or  on  the  chin- 
olin  group  cannot  yet  be  decided  with  certitude.  The  fact  that  the 
bodies  obtained  from  apoquinia  and  apoquinidia  show  no  fluorescence 
in  sulphuric  acid  solution  would  perhaps  indicate  that  hereby  the  oxy- 
methylchinolin  group,  which  evidently  causes  the  fluorescence  of  the 
bases  in  question,  becomes  altered. 
It  is  worthy  of  notice  that  hydrochlorapocinchonia  in  sulphuric 
acid  solution  is  attacked  with  great  difficulty  by  potassium  ])erman- 
ganate,  and  we  have,  therefore,  possibly  in  this  body  a  substance  with 
a  closed  chain  of  atoms. 
The  author  considers  it,  therefore,  very  probable  that  the  hydrocin- 
chonia  of  Caventou  and  Willm,  which  Skraup  now  calls  cinchotin,  is 
likewise  a  body  with  a  closed  chain  of  atoms,  a  true  hydroderivative 
of  cinchonia,  and,  for  the  reason  just  stated,  offers  greater  resistance 
to  oxydation  than  the  cinchonia  itself. 
The  formation  of  diapocinchonia  by  the  action  of  hydrochloric 
acid  upon  apocinchonia  may  be  caused  by  apocinchonia  showing  a 
