Am.  Jour.  Pharm. 
Jan  ,1889. 
Isatropylcocain  e. 
35 
stream  of  air  for  several  days  at  the  ordinary  temperature,  and  finally 
at  45°. 
The  alkaline  filtrate  from  the  alkaloid  contains  ecgonine,  the  quantity 
of  which  is  from  1  to  2  per  cent,  of  the  crude  material. 
Isatropylcocainc  is  very  similar  to  cocaine,  but  both  the  base  and  its 
salts  are  amorphous,  and  the  former  is  not  so  readily  soluble  in  ammo- 
nia and  light  petroleum  as  cocaine.  It  is  easily  soluble  in  cold  alco- 
hol, ether,  benzene  and  chloroform,  but  only  very  sparingly  in  light 
petroleum,  and  in  all  cases  a  resinous  mass  is  obtained  when  the  sol- 
vent is  evaporated.  It  begins  to  soften  at  65°,  but  has  no  definite 
melting  point ;  at  90-100°  it  loses  water  slowly,  and  at  120°  it  turns 
brown  and  is  gradually  decomposed.  All  the  salts  are  amorphous  and 
soluble  in  water.  Picric  acid  produces  a  yellow,  chromic  acid  an 
orange,  and  potassium  permanganate  a  violet  precipitate,  which  changes 
to  brown.  The  chlorides  of  mercury,  tin,  gold  and  platinum,  and  most 
of  the  usual  reagents  for  alkaloids,  also  give  amorphous  precipitates. 
The  alcoholic  solution  does  not  show  an  alkaline  reaction  with  phe- 
nolphthalein,  and  is  dextrorotatory. 
The  base  is  a  powerful  poison,  but  its  action  is  not  similar  either  to 
that  of  cocaine  or  atropine ;  the  symptoms  of  poisoning  sometimes  ob- 
served after  the  administration  of  impure  cocaine  may  be  due  to  this 
alkaloid. 
Methyl  chloride  is  evolved  when  the  base  is  heated  with  concentrated 
hydrochloric  acid,  and  when  boiled  with  strong  hydriodic  acid  methyl 
iodide  is  obtained,  the  quantity  of  which,  estimated  by  ZeiseFs  method, 
showed  that  one  methyl-group  has  been  eliminated.  It  is  also  decom- 
posed, with  separation  of  methyl  alcohol,  when  heated  for  a  long  time 
with  dilute  sulphuric  acid,  but  no  ethyl  alcohol  is  formed.  When 
boiled  for  about  an  hour  with  hydrochloric  acid,  sp.  gr.  1*1,  it  is  decom- 
posed into  methyl  alcohol,  ecgonine,  and  isatropic  acid  in  molecular 
proportions,  as  in  the  following  equation  : 
C19H23N04+2H20-:CH40+C9H15N03+C9H802. 
The  product  of  the  reaction  is  filtered  and  the  two  isatropic  acids  in 
the  residue  separated  by  means  of  their  barium  salts. 
f-Isatropic  acid,  C9H802,  forms  about  two-thirds  of  the  residue.  It 
crystallizes  from  50  per  cent,  alcohol  in  small,  colorless  needles,  melts 
at  274°,  and  is  soluble  in  hot  glacial  acetic  acid,  but  only  very  spar- 
ingly in  ether,  benzene  and  carbon  bisulphide.    The  barium  salt, 
