AmAp?u!i897arm'}    Marrubiin  and  its  Dichlorine  Derivative.  205 
Morrison  further  states  that  his  results  indicate  the  composition 
of  marrubiin  to  be  very  close  to  that  of  absinthiin,  C40H58O9,  a  crys- 
talline bitter  principle  obtained  from  wormwood,  and  described  by 
Kromayer  in  Archivder  Pharrnacie,  No.  108,  p.  120,  but  that  it  does 
not  agree  with  all  the  properties  described  by  Kromayer,  who  states 
that  absinthiin  melts  at  1200  to  125°  C. 
Thus  far  I  have  reviewed  the  history  of  marrubiin,  and  described 
the  investigations  and  results  of  preceding  workers.  I  shall  now 
detail  my  own  experience  with  the  extraction  of  marrubium,  for  the 
isolation  and  purification  of  marrubiin,  and  describe  the  properties 
of  that  substance  as  observed  by  myself. 
The  herb  was  collected  by  the  writer  at  Lawnside,  N.  J.,  in  the 
months  of  July,  August  and  September,  1896.  It  was  carefully 
dried  in  a  room,  without  exposure  to  direct  sunlight.  The  herb 
was  then  finely  ground,  and  trial  extractions  made  with  alcohol, 
benzol  and  acetone  as  menstrua,  500  grammes  of  the  herb 
being  subjected  to  the  solvent  action  of  each  of  the  solvents  named. 
Of  the  three  different  menstrua  mentioned,  acetone  was  found  to  be 
the  most  satisfactory  one,  extracting  the  largest  quantity  of  the 
bitter  principle  and  the  least  amount  of  foreign  matter,  with 
smallest  quantity  of  menstruum. 
Two  and  a  half  kilogrammes  of  the  herb  were  now 
extracted  with  acetone,  the  acetone  being,  from  time  to  time,  recov- 
ered from  the  extract,  and  used  again  as  menstruum.  When  the 
herb  was  practically  exhausted,  the  acetone  was  recovered  from  the 
extract,  by  distillation,  and  the  thick,  syrupy  mass  which  was  left 
was  treated  repeatedly  with  hot  benzol.  The  benzol  solution  was 
allowed  to  stand  for  twenty-four  hours  for  marrubiin  and  resinous 
matter  to  separate.  The  mother  liquid  was  then  poured  off,  and 
the  residue  treated  with  a  fresh  portion  of  hot  benzol  and  allowed 
to  stand  as  before.  This  treatment  was  continued  until  relatively 
pure  crystals  of  a  yellowish  color  were  obtained.  The  crystals  were 
then  repeatedly  crystallized  from  hot  alcohol,  by  solution  and  chill- 
ing, which,  owing  to  the  prevalent  cool  weather,  afforded  a  rapid 
means  of  crystallization.  They  still  retained  a  slight  yellow  tinge, 
which,  however,  was  removed  by  treating  them  with  animal  char- 
coal. A  portion  of  the  syrupy  mass  obtained  above,  on  distilling 
off  the  acetone,  was  treated  repeatedly  with  hot  alcohol,  and  allowed 
to  stand  for  twenty-four  hours  after  each  treatment,  without  previous 
