Aro.  Jour.  Pharm. 
April,  1889. 
Alkaloids  of  the  Areca  Nut. 
191 
ing  matter,  etc.,  remained  undissolved.  After  filtration  the  alkaloidal 
solution  was  evaporated  to  a  small  volume,  treated  with  sufficient 
caustic  baryta,  and  shaken  repeatedly  with  ether,  which  removed  a 
base  that  has  been  named  "  arecoline,"  on  account  of  its  oil-like  char- 
acter. The  residual  liquid,  which  beside  alkaloidal  hydriodides,  con- 
tained some  barium  iodide,  was  neutralized  with  sulphuric  acid,  and 
the  alkaloids  were  set  free  by  treatment  successively  with  silver  sul- 
phate, caustic  baryta  and  carbonic  acid.  The  solution  of  the  pure 
alkaloids  was  evaporated  to  dryness  and  the  residue  exhausted  with 
cold  absolute  alcohol  (or  chloroform).  "  Arecaine  "  remained  undis- 
solved, whilst  a  third  alkaloid,  together  with  coloring  matter,  etc.,  went 
into  solution,  and  upon  evaporation  of  the  alcohol  remained  as  an 
amorphous  mass. 
According  to  the  second  method  the  powdered  areca  nuts  were 
exhausted  cold  with  milk  of  lime,  the  filtered  extracts  neutralized 
with  sulphuric  acid  and  evaporated  to  a  syrupy  consistence.  By  dis- 
solving in  a  little  water  and  filtering,  the  gypsum  and  separated  color- 
ing matter  were  removed  ;  the  solution  was  then  again  concentrated, 
made  alkaline,  and  the  areGoline  shaken  out  with  ether.  The  other 
bases  were  then  precipitated  as  before  with  potassium-bismuth  iodide 
and  sulphuric  acid. 
The  yield  of  arecoline  amounted  to  0*07 — or  at  most  0*1 — per 
cent. ;  that  of  arecaine  to  0*1  per  cent.  Only  a  very  small  quantity  of 
the  third  alkaloid  was  obtained. 
Arecoline  (C8H13N02). — The  arecoline  was  withdrawn  from  the 
ether  solution  obtained  as  described  by  shaking  it  with  acidulated 
water,  the  neutralized  liquid  evaporated  to  a  small  volume  and  after 
adding  sufficient  potash  solution  again  shaken  out  with  ether.  The 
base  left  upon  evaporation  of  this  solution  was  neutralized  with  hydro- 
bromic  acid,  and  the  dried  salt  perfectly  purified  by  repeated  recrys- 
tallization  from  absolute  alcohol.  From  this  purified  compound  the 
free  base  and  other  salts  of  it  were  prepared. 
Arecoline  forms  a  colorless  oily  liquid  of  strongly  alkaline  reaction, 
which  is  soluble  in  all  proportions  in  water,  alcohol,  ether  and  chloro- 
form. It  is  volatile  and  can  be  distilled,  the  boiling  point  appearing 
to  be  about  220°  C,  though  this  could  not  be  determined  with  cer- 
tainty, on  account  of  insufficiency  of  material.  The  salts  are  easily 
soluble,  some  of  them  deliquescent,  but  mostly  crystallizable.  It 
gives  with  potassium-bismuth  iodide  a  pomegranate  red  precipitate, 
