448 
Jaborandi  and  Its  Alkaloids. 
/  Am.  Jour.  Pharrr . 
X      August,  18£6. 
leaves  yield  four  bases — pilocarpine,  pilocarpidine,  jaborine  and  jabo- 
ridine,  the  two  latter  being  formed  respectively  from  the  two  former. 
Hardy  and  Calmels,1  on  the  contrary,  consider  that  pilocarpidine  is 
not  a  natural  constituent  of  the  leaves,  but  a  product  of  the  altera- 
tion of  pilocarpine,  effected  in  the  extraction,  while  they  question  the 
existence  of  jaboridine.  But  the  definition  of  all  these  bases  is  de- 
fective. The  pilocarpidine  of  Harnack  is  said  to  form  a  finely  crys- 
tallizable  nitrate,  but  Hardy  and  Calmels  state  that  the  pilocarpidine 
produced  by  them  from  pilocarpine  gives  "  basic  salts  that  exactly 
resemble  those  of  pilocarpine,"  but  are  "  gummy."  Additional  un- 
certainty has  been  produced  by  inaccuracy  in  the  published  abstracts 
of  original  memoirs  ;  thus,  for  instance,  the  abstract  of  Hardy  and 
Calmels'  paper  in  the  Journal  of  the  Chemical  Society2,  states  that 
nitric  acid  "  has  no  action  on  pilocarpine,"  whereas,  the  original 
says  that  it  has  only  the  effect  of  converting  it  into  pilocarpidine.3 
In  order  to  ascertain  whether  the  differences  of  melting  point  ob- 
served in  the  nitrate  obtained  by  recrystallization,  as  well  as  in  com- 
mercial samples  of  the  salt,  were  due  to  alteration  of  pilocarpine, 
we  submitted  several  portions  to  the  action  of  heat,  which  is  stated 
to  have  the  effect  of  converting  pilocarpine  into  jaborine,  and  also 
into  pilocarpidine.  In  operating  upon  the  salt  described  as  "  pure 
pilocarpine  nitrate,"  and  melting  at  14170  C,  we  found  that,  after 
being  heated  in  solution  for  fourteen  hours  in  contact  with  air,  there 
was  a  reduction  of  the  melting  point  to  1 330.  The  salt  was  still  crys- 
talline, and,  on  recrystallization  from  alcohol,  it  was  separated  into 
two  portions:  one,  crystalline,  amounting  to  80  per  cent,  of  the  original 
quantity,  melted  at  138-2°,  while  the  other  was  gummy,  and  con- 
tained a  base  insoluble  in  water.  Evidently  the  alteration  in  this 
case  was  only  partial. 
Another  portion  of  the  same  salt  was  recrystallized  from  alcohol 
in  fractions,  but  without  any  considerable  alteration  in  the  original 
melting  point  being  effected,  as  in  the  case  of  nitrate  obtained  from 
the  samples  of  jaborandi  leaves  in  the  experiments  above  described. 
In  connection  with  the  high  melting  point  of  one  of  the  samples 
of  commercial  nitrate,  for  which  we  are  indebted  to  the  kindness  of 
Mr.  Martindale,  it  is  of  interest  to  mention  that,  when  administered 
1  Compt.  Rend.,  103,  11 16. 
2 Jour.  Chem.  Soc,  50,900. 
3  Compt.  Rend.,  103,  1562. 
