Am.  Tour.  Pharm.  ) 
May,  1921.  5 
The  Quinotoxin  Myth. 
339 
linking  CHOH  in  c  is  hydrolized  to  CO,  the  H  being  transferred  to 
the  adjacent  C  and  N  of  the  loipon,  forming  an  imid  group,  and 
breaking  the  benzene  ring,  according  to  this  schema : 
CH 
\ 
\ 
CH2    CH2    CH2  —  CH  —  CH2 
CH3O.C9H5N  —  CHOH  —  CH     CH2  CH2 
\ 
\ 
N 
/ 
(quinine)  becomes : 
CH 
/ 
/ 
\ 
\ 
CH2    CH2    CH  —  CH  —  CH2 
CH3O.C9H5N  —  CG  —  CH2    CH2  CH2 
\ 
NH 
(quinicin) 
Formation  of  Quinicin  and  Cinchonicin  by  Acids. — Pasteur 
prepared  quinicin  by  heating  quinine  with  dilute  sulphuric  acid  at 
120  C.  At  100,  however,  Biddle  2  found  that  dilute  mineral  acids 
(to  normal)  convert  only  from  2  to  3  per  cent,  of  the  cinchonine, 
while  weak  organic  acid  (acetic,  etc.,  ten-thousandth  normal)  trans- 
form 95  per  cent.  The  conversion  is  independent  of  the  dilution  or 
dissociation.  Similar  results  were  obtained  independently  by  Rabe.3 
At  from  36  to  38  C.  the  conversion  proceeds  very  slowly,  even 
with  organic  acids,  so  that  at  most  from  0.2  to  1  per  cent,  are  con- 
verted in  forty-eight  hours.  The  concentration  of  cinchonicin  prob- 
ably does  not  increase  with  longer  heating,  for  there  is  a  parallel 
transformation  of  cinchonicin  into  an  insoluble  resin. 
Some  conversion  into  cinchonicin  occurs  also  in  sunlight,  and 
2  Biddle,  H.  C. :  J.  Am.  Chem.  Soc.  34 :  500,  1912. 
3  Rabe :  Ber.  d.  chem.  Gesellsch.  43  :  3308,  1910. 
