^"Ma^'iss?™"}  Gelsemine  and  Crystalline  Salts.  257 
and  particularly  noticed  that  the  published  processes  for  its  extraction 
did  not  yield  a  product  that  could  be  called  pure,  as  it  was  more  or  less 
colored  yellow  or  brown.  I  also  observed  that  traces  of  gelseminic 
acid  persistently  adhered  to  the  alkaloid,  as  evidenced  by  the  fluores- 
cence of  the  latter  in  the  presence  of  alkalies.  At  this  time  I  was 
strongly  impressed  with  the  above  defects,  and  doubted  not  that  if 
gelseminia  could  be  obtained  in  a  sufficient  state  of  purity  (possessed  as 
it  is  of  such  strongly  basic  characters)  its  salts  could  be  made  to  crys- 
tallize. The  small  quantity  of  alkaloid  at  my  command  did  not  admit 
of  many  experiments,  and  these  were  without  result.  Later  on,  I  pre- 
pared the  alkaloid  in  small  quantity,  and  obtained  one  of  its  salts  in 
microscopic  crystals,  sufficiently  well  defined  to  determine  me  to  make 
an  investigation  on  a  larger  portion  of  material.  I  am  now  able  to 
state  I  have  prepared  in  the  crystalline  form  the  pure  alkaloid  and  a 
number  of  its  salts. 
Method  of  Extraction. — Twelve  kilograms  of  well-powdered  root 
were  exhausted  with  alcohol,  which  left  after  distillation  1703  grams 
of  soft  extract.    The  extract  on  resting,  separated  into  two  strata. 
The  superstratum,  green  in  color  and  having  the  appearance  of  an 
oleo-resin,  was  repioved  and  found  to  be  practically  insoluble  in  water ; 
it  was  well  shaken  with  dilute  hydrochloric  acid  to  remove  traces  of 
adhering  alkaloid,  and  the  said  solution  mixed  with  the  substratum. 
The  substratum,  containing  the  alkaloid,  was  diluted  with  Avater  until 
it  ceased  to  precipitate  resin,  and  left  a  clear  bright  brown  solution 
which  was  evaporated  at  a  temperature  below  60°C.,  treated  with  am- 
monia in  excess  and  thoroughly  washed  with  ether.  The  ether  solu- 
tion, now  containing  the  gelsemine  and  beautifully  fluorescent  from  the 
presence  of  gelseminic  acid,  was  decanted  and  exposed  a  short  time  to 
allow  excess  of  ammonia  to  escape.  Hydrochloric  acid  was  next  added 
in  fractions  with  agitation  until  the  fluorescence  was  destroyed,  a  cer- 
tain indication  that  the  whole  of  the  alkoloid  had  been  removed  from 
the  ether.  The  hydrochloride  of  gelsemine  had  now  separated  from 
the  ether,  forming  a  layer  of  pale  yellow  amorphous  precipitate,  which 
upon  separation  was  subjected  to  several  reconversions,  until  the  last 
traces  of  color  and  fluorescence  had  disappeared,  the  product  being  20*2 
grams  of  perfectly  white  hydrochloride  of  gelsemine.  It  may  here  be 
mentioned  that  the  pure  alkaloid  obtained  from  the  hydrochloride  by 
alkali,  and  chloroform  or  ether,  holds  its  solvents  tenaciously,  and 
requires  the  heat  of  a  water-bath  to  eflectually  remove  them.  During 
17 
