338 
The  Quino  toxin  Myth. 
Am.  Jour.  Pharm. 
May,  1921. 
"quinotoxin"  a  misnomer. 
The  name  "quinotoxin"  is  probably  in  part  responsible  for  the 
misconceptions.  It  is  incorrect  historically,  suggests  false  theories, 
and  leads  to  confusion  with  another,  quite  different,  substance.  It 
should  be  abandoned,  and  displaced  by  the  perfectly  good  name  be- 
stowed on  it  by  its  original  discoverer.  Pasteur,  in  1853,  first  pre- 
pared this  substance  and  a  corresponding  derivative  of  cinchonin, 
and  named  them  chinicine  and  chichonicine.  The  terms  chinotoxin 
and  cinchotoxin  (and  chinatoxins,  collectively)  were  applied  forty 
years  later  by  Miller  and  Rohde,1  who  prepared  these  derivatives  by 
a  lightly  different  method.  In  this,  they  disregarded  not  only  the 
fact  that  these  substances  had  already  received  a  name,  but  also  the 
fact  that  the  name  chinatoxin  had  been  applied  eleven  years  previ- 
ously by  Ostermayer  (1884)  to  an  entirely  different  substance 
(diquinolin-dimethylsulphate).  This  is  likely  to  lead  to  serious  con- 
fusion. The  anglicized  terms  of  Pasteur  will,  therefore,  be  used  ex- 
clusively in  the  following  discussion. 
CHEMICAL  RELATION  OF  QUINICIN  AND  CINCHONICIN  TO  QUININ 
AND  CINCHONIN. 
The  structure  of  the  cinchona  alkaloids  is  not  fully  understood, 
as  they  have  not  been  synthetized.    It  is  fairly  complex.    That  of 
...  ,      CH3O.C9H5N.  CHOH.  C9H14N. 
qumin  may  be  expressed  as      ^     ^         ^  ^ 
It  includes  a  quinolin  ring  (b),  to  which  are  attached  in  the  para 
positive  a  methoxyl  (a),  and  a  pyridin  derivative  ("lbipon")  (d), 
through  a  CHOH  linkage  (c).  Replacement  of  the  methoxyl  by 
other  alkyl  groups  does  not  destroy  the  action,  but  may  even  fortify 
it  (Frankel  Arzeneimittelsynthese) .  Omission  of  the  group,  how- 
ever, greatly  weakens  the  antimalarial  efficiency,  but  increases  the 
. ..        f.  H.C9H5N.CHOH.C9H14N. 
convulsive  action.    This  is  cinchonin,   ^     ^     ^  ^ 
Replacement  of  the  CH3OH  by  OH  gives  cuprein. 
Quinicin  and  cinchonicin  are  formed  when  quinin  or  cinchonin 
are  heated  with  acids.  They  have  the  same  elementary  formulas  as 
quinin  and  cinchonin ;  but  a  rearrangement  has  occurred  in  the  loipon 
and  connecting  link  (d)  and  (c).    It  is  generally  believed  that  the 
1  Miller,  W.  von,  and  Rohde :  Ber.  d.  chem.  Gesellsch.  28  :  1056,  1895. 
