330  Developments  in  Organic  Compounds. 
July.  1901. 
erroneous,  hence  such  synthesized  substances  differed  essentially 
from  this  alkaloid.  Of  all  the  synthetic  antipyretics  none  possess 
the  most  important  function  of  quinin,  that  is,  its  specific  action  in 
malaria.  Quinolin 
N 
being  the  mother  substance  of  quinine,  was  necessarily  the  basis  of 
these  attempts.  Filehne  found  that  only  the  alkylated  nitrogen  of 
a  tetrahydro  quinolin  was  worthy  of  trial ;  following  this  came 
Fischer's  Kairin,  Kairolin  and  Skraup's  Thalline 
H2 
Kairin  //Xv/X  H2 
(ethyl-ortho-oxy-quinolin  tetra  hydride).  ^2 
OH   N  —  C2H5HCl 
Owing  to  the  unpleasant  and  sometimes  dangerous  toxic  side 
actions  this  class  of  derivatives  has  been  dropped.  This  nucleus  fur- 
nishes us,  however,  a  valuable  antiseptic  in  Loretin  (meta-iodo.ortho- 
oxy-quinolin-ana-sulfonic  acid). 
SOoH 
OH  N 
With  the  intention  to  produce  a  quinine-like  body  Knorr  discovered 
antipyrin.  This  investigator's  views  as  to  the  constitution  of  this 
synthesized  body  were  at  first  erroneous.  Knorr  thought  that  this 
newly  discovered  body  was  a  di-methyl-oxy-chinizin  in  which  two 
quinolin  molecules  were  linked  to  the  pyridin  nucleus,  as  was  sup- 
posed to  be  the  case  with  quinin.  Later  it  was  found  that  the 
five-membered  ring  Pyrazol 
NH 
\ 
N 
CH 
HC 
CH 
