258  The  Chemistry  of  Ipecacuanha.  {*m'$£?:uMXm' 
Solutions  of  the  alkaloids  in  alcohol,  chloroform,  benzene  or  ether, 
also  become  colored  on  exposure  to  light,  with  formation  of  a  reddish- 
colored  deposit.  The  salts  of  both  alkaloids,  on  the  contrary,  do  not 
appear  to  undergo  similar  alteration,  but  in  a  pure  state  remain 
perfectly  colorless  when  exposed  to  light. 
Since  the  publication  of  the  last  paper  on  ipecacuanha  a  third 
alkaloid — the  probable  existence  of  which  has  already  been  indi- 
cated— has  been  isolated  in  small  quantity.  It  exists  in  the  drug  in 
very  small  amount  relatively  to  emetine  and  cephaeline,  and  it  dif- 
fers from  those  alkaloids  in  being  very  sparingly  soluble  in  ether. 
This  alkaloid  is  soluble  in  alkaline  liquids,  and  it  remains  in  the 
ammoniacal  liquor  from  which  emetine  and  cephaeline  have  been 
extracted  by  shaking  with  ether.  It  was  extracted  from  that  liquor 
by  shaking  with  chloroform.  The  quantity  obtained  as  yet  was  too 
small  to  admit  of  complete  examination,  but  the  physical  characters 
of  this  alkaloid  distinguish  it  in  a  very  definite  manner.  It  is  a  crys- 
tallizable  substance  obtainable  by  slow  evaporation  of  an  ether 
solution  in  well-defined  transparent  prisms  of  a  pale  lemon-yellow 
color.  It  melts  at  about  138°  C,  neutralizes  acids,  and  apparently 
has  a  much  higher  molecular  weight  than  emetine  or  cephaeline. 
It  dissolves  readily  in  alcohol  or  chloroform,  the  solutions  becoming 
dark-colored  on  exposure  to  light  and  depositing  a  dark  brown 
substance. 
The  failure  of  most  previous  observers  to  arrive  at  correct  con- 
clusions in  regard  to  the  alkaloids  of  ipecacuanha  presents  some 
collateral  features  of  interest,  inasmuch  as  it  shows  how  largely  the 
results  of  such  investigation  may  be  determined  by  accidental  cir- 
cumstances. The  extraction  of  ipecacuanha  with  chloroform  in  the 
presence  of  caustic  potash,  adopted  by  Lefort,  naturally  furnished  a 
product  consisting  of  a  mixture  of  all  the  alkaloids,  and  in  the 
absence  of  any  ascertained  distinction  between  them  their  separation 
was  impossible.  Hence  the  formula  assigned  to  emetine  by  that 
observer,  on  the  basis  of  Dumas'  analysis,  was  inaccurate.  In  the 
subsequent  investigation  by  Lefort  and  Wurtz  the  result  arrived  at 
was  defective  for  the  same  reasons,  although  the  mixed  alkaloids 
were  then  obtained  in  a  condition  of  greater  freedom  from  impurity 
by  extracting  the  drug  with  ether  in  presence  of  lime. 
The  result  obtained  by  Podwyssotzki,  by  using  ferric  chloride  to 
get  rid  of  the  tanni  constituent,  was  vitiated  by  the  use  of  petro- 
