20  Constitution  of  the  Alkaloids.  {ATanuaryPimm' 
and  the  latter  of  Goldschmidt.    Cocaine  was  isolated  by  Niemann, 
in  i860,  and  its  formula  determined  by  Lossen,  but  Einhorn  first, 
in  1888,  determined  that  it  was  an  ester,  i.  e.,  methyl.benzoyl  ecgo- 
nine,  and  further  determined  that  ecgonine  was  methyl-tetrahydro- 
pyridyl-/2-oxypropionic  acid,  and  that  hence  cocaine  is  the  methyl 
ester  of  methyl-tetrahydro-pyridyl-/?-benzoyl-propionic  acid. 
H2 
C 
/\ 
HC       CH2       CH2— COOCH, 
I         I  I 
HC 
N 
CH3  Cocaine. 
At  about  this  time  also  pilocarpine  was  being  studied  by  Hardy, 
in  Paris,  he  also  first  having  isolated  the  alkaloid  in  1874,  and  he 
worked  out  the  constitution,  and  then  made  a  successful  synthesis 
of  the  same.  He  found  it  was  Betain  or  inner  salt  of  j9-pyridine 
lactic  acid. 
CH  CH, 
HC       C  C  N  (CH3) 
I         I         I  I 
HC       CH     CO — O 
N 
Pilocarpine. 
In  1890  the  constitution  of  hydrastine  was  worked  out  by  Freund 
and  Phillips,  who  were  aided  in  their  work  by  the  fact  that  Roser  had 
not  long  previously  worked  out  the  constitution  of  the  very  similar 
alkaloid  narcotine.    This  is  an  iso-quinoline  derivative. 
CH3 
O 
I 
HC  C.OCH3 
I  I 
HC  C.CO 
C 
I 
CH— O 
CH  CH 
CH3N       C  CO 
f  I 
C  CO 
>H2 
CH2  CH 
Hydrastine. 
