AnAp°riU897arm'}    Marrubiin  and  its  Dichlorine  Derivative.  20 1 
MARRUBIIN  AND  ITS  DICHLORINE  DERIVATIVE. 
By  Harry  Matusow. 
Contribution  from  the  Chemical  Laboratory  of  the  Philadelphia  College  of 
Pharmacy.    No.  163. 
This  crystallizable  principle,  obtained  from  Marrubium  vulgare, 
a  plant  belonging  to  the  natural  order  Labiatae,  was  first  isolated  by 
Mein  in  1855,  and  investigated  by  Harms,  to  whom  the  former  pre- 
sented it  for  investigation. 
Harms  (Archiv  der  Pharmacie,  No.  83,  p.  144,  August,  1855), 
then,  upon  investigation,  ascribed  to  marrubiin  the  following  prop- 
erties : 
"  Marrubiin  forms  stellate  groups  of  colorless  needles ;  it  melts 
at  1480  C,  and  at  a  higher  temperature  it  breaks  up  with  the 
development  of  an  unbearable  odor ;  it  is  almost  insoluble  in  water, 
easily  soluble  in  alcohol — particularly  in  hot  alcohol — and  soluble 
in  ether.  Its  taste  is  persistently  bitter  ;  and  it  possesses  a  tend- 
ency to  become  colored  when  exposed  to  the  air." 
The  next  investigator  to  take  up  the  subject  was  Kromayer 
(Archiv  der  Pharmacie,  No.  108,  p.  258,  1861),  who  extracted  the 
plant  with  boiling  water  precipitated  the  infusion  with  lead 
acetate,  removed  the  excess  of  lead  with  hydrogen  sulphide,  and 
then  concentrated  the  infusion  to  a  syrupy  consistence.  He  then 
obtained  the  crystals  from  the  infusion  by  means  of  alcohol  and 
purified  them  by  treating  with  animal  charcoal. 
Kromayer's  results,  which  were  published  simultaneously  with 
the  process  of  extraction  briefly  described  above,  were  as  follows  : 
"  From  ethereal  solutions  it  crystallizes  in  colorless  rhombic 
plates,  or  thick,  four-sided,  double,  gypsum-like  crystals. 
"  From  alcoholic  solutions  it  crystallizes  in  needles. 
"  The  crystals  are  gritty  between  the  teeth.  On  account  of  their 
sparing  solubility  in  water,  their  bitter  taste  is  not  perceived  until 
after  being  kept  in  the  mouth  for  some  time. 
"  Alcohol  or  ether  dissolves  it  readily. 
"  The  alcoholic  solution  tastes  intensely  bitter,  and  has  a  some- 
what acrid  after-taste. 
"  The  alcoholic  solution  reacts  perfectly  neutral.  Almost  com- 
pletely insoluble  in  cold  water  and  only  sparingly  soluble  in  hot 
water. 
"  The  hot-water  solution  of  marrubiin  tastes  strongly  bitter. 
