550  An  Alkaloid  obtained  from  Jaborandi.  { Am-D{T"'J7tTtn' 
ON  AN  ALKALOID  OBTAINED  FROM  JABORANDI,  ITS  PLATINIC 
COMPOUND,  AND  THEIR  FORMULA. 
BY  CHARLES  T.  KINGZETT. 
In  1875  an  alkaloid  was  isolated  from  the  leaves  and  stalks  of  jabo- 
randi (Pilocarpus  pennatifolius,  of  Lemaire),  almost  simultaneously  and 
quite  independently  by  Mr.  A.  W.  Gerrard  and  M.  Hardy  ("  Amer, 
Jour.  Phar.,  1875,  pp.  214  and  315).  There  is  another  kind  of 
jaborandi,  a  species  of  Piper,  from  which  Parodi  has  isolated  an  alkaloid 
of  the  formula  C20H12N2O6. 
To  the  alkaloid  upon  which  M.  Gerrard  worked,  the  name  of  pilo- 
carpina  has  been  given.  He  has  detailed  the  methods  of  extraction, 
and  states  that  it  forms  crystallizable  salts  with  hydrochloric,  nitric 
and  sulphuric  acids.  He  further  exhibited  some  crystals  of  the 
so-called  hydrochloride  in  a  dark-brown  mother-liquor,  at  the  last  meeting 
of  the  Pharmaceutical  Conference,  but  neither  at  that  time  nor  since 
has  he,  or  M.  Hardy,  or  any  other  observer,  "published  any  formulae 
for  the  alkaloid  or  its  compounds.  Mr.  Gerrard  has  further  stated 
his  opinion  that  there  are  at  least  two  alkaloids  in  jaborandi,  and  that 
the  one  upon  which  he  worked  gave  no  precipitate  with  phospho- 
molybdic  acid.  Several  other  papers  relating  to  this  subject  will  be 
found  in  the  "  Year  Book  of  Pharmacy"  for  1875. 
More  recently  Hardy  states  that  he  has  obtained  from  the  distillate 
of  an  aqueous  extract  of  the  leaves  of  jaborandi  a  quantity  of  crude 
oil,  containing  a  terpene  which  gave  a  crystalline  di-hydrochloride* 
But  the  boiling  point  of  1780  C,  which  he  attributes  to  the  hydrocar- 
bon, would  rather  point  to  cymene  than  to  a  terpene.  He  also  obtained 
a  solid,  colorless  substance,  which  was  not  further  examined  ("  L'Union 
Pharmaceutique,"  vol.  xvi,  p.  365).  My  first  experiment  was  conducted 
upon  the  leaves  of  the  plant.  These  were  thoroughly  extracted  with 
water  of  700  C,  and  the  extract  concentrated  to  a  small  bulk,  filtered 
from  deposited  matters,  rendered  acid  by  hydrochloric  acid,  and  fully 
precipitated  with  phosphomolybdic  acid.  The  bright  yellow  precipi- 
tate, after  thorough  washing,  was  decomposed  after  the  method  of 
Sonnenschein,  that  is  by  heating  with  excess  of  baryta,  and  the  excess 
of  barium  was  removed  by  carbonic  acid.  The  filtrate  was  strongly 
alkaline,  and  was  found  to  contain  barium.  This  barium  was  carefully 
removed  by  sulphuric  acid,  and  the  filtrate,  which  gave  the  character- 
istic reactions  of  an  alkaloid  with  various  reagents,  was  converted  into 
