64 
Chemistry  of  Ipecacuanha. 
f  Am.  Jour.  Pharru. 
(.   February,  1901. 
more  freely  by  heating.  By  rapid  evaporation  of  a  concentrated 
ether  solution  of  the  base  distinct  acicular  crystals  were  sometimes 
obtained.  When  free  from  moisture  or  adherent  petroleum  ether, 
it  melted  at  68°-74°  C. 
The  retention  of  minute  traces  of  solvent  was  also  considered  to 
have  been  the  cause  of  the  differences  between  the  analytical  results 
of  previous  observers,  and  when  that  was  provided  against,  analysis 
gave  numbers  leading  to  the  formula  C30H40NoO5. 
In  none  of  the  memoirs  above  referred  to  is  there  any  statement 
as  to  the  kind  of  ipecacuanha  operated  on,  and  it  was  probable  that 
some  of  the  discrepancies  they  present  might  be  ascribed  to  differ- 
ences in  the  drug  examined.  The  general  probability  that  ipecacu- 
anha might  contain  more  than  one  alkaloid  was  also  recognized  by 
Glenard  as  well  as  by  Lefort  and  Wurtz,  but  in  neither  case  was  any 
definite  conclusion  arrived  at  on  that  point,  so  that  the  alkaloid  ob- 
tainable from  ipecacuanha  has  hitherto  been  always  regarded  as  one 
substance,  having  distinct  chemical  individuality. 
On  the  contrary,  we  find  that  ipecacuanha  resembles  cinchona 
bark,  a  product  of  the  same  natural  order,  containing  at  least  three 
alkaloids,  and  probably  other  alkaloids  in  small  proportions. 
Of  the  three  alkaloids  which  we  have  isolated,  one  is  uncrystal- 
lizable,  but  capable  of  forming  salts  which  are  crystalliz  xble,  though 
for  the  most  part  very  freely  soluble.  For  this  base  we  have  re- 
tained the  name  emetine.  The  second  alkaloid,  named  cephaeline, 
is  crystallizable,  less  soluble  in  ether  than  emetine,  but  freely  solu- 
ble in  alcohol  or  chloroform;  much  more  soluble  than  emetine  in 
hot  petroleum  spirit,  and  readily  soluble  in  solutions  of  caustic 
alkali.  The  third  alkaloid,  termed  psychotrine,  has  been  isolated  in 
only  small  quantity,  and  exists  in  the  drug  in  very  small  amount, 
relatively,  to  emetine  and  cephaeline. 
The  failure  of  most  previous  observers  to  arrive  at  correct  conclu- 
sions in  regard  to  the  ipecacuanha  alkaloids  presents  some  features 
of  interest  as  showing  how  largely  the  results  of  such  investigation 
may  be  influenced  by  accidental  circumstances. 
Lefort's  method  of  extraction  with  chloroform  in  the  presence  of 
caustic  potash  furnished  a  product  consisting  of  an  uncertain  mix- 
ture of  all  the  alkaloids,  and,  in  the  absence  of  any  ascertained  dis- 
tinction between  them,  their  separation  by  Lefort  was  impossible. 
Therefore,  the  formula  assigned  to  emetine  by  Lefort,  on  the  basis  of 
