108 
Active  Constituents  of  Podophyllin. 
f  Am.  Jour.  Pharm. 
\      Mar.,  1882. 
nia,  for  the  purpose  of  neutralization,  it  was  observed  that  the  snow- 
white  crystals  remained  undissolved,  while  the  ammonia  solution  became 
neutral.  The  liquid  portion  was  warmed  upon  the  water-bath,  and 
after  the  removal  of  the  last  traces  of  water,  the  free  ammonia  is  not 
only  volatilized,  but  also  that  in  combination  with  the  organic  acid 
of  the  podophyllotoxin,  so  that  the  reaction  again  becomes  acid.  The 
latter  substance  is  nearly  colorless,  and  forms,  after  drying  completely, 
horn-like  laminae  or  granules,  which  are  readily  soluble  in  even  very 
dilute  alcohol,  in  ether  and  chloroform,  but  in  Avater  only  by  the  aid 
of  heat.  These  laminae  or  granules  are  picroyodophyllinic  acid ;  in 
the  latter  the  crystallized  picropodophyllin  dissolves,  whereby  the 
above-mentioned  gelatinous  liquids  are  formed,  as  also  the  spheroidal 
forms  with  the  enclosed  crystals.  From  these  artificial  solutions  the 
crystallized  picropodophyllin  can  again  be  obtained.  Picropodophyl- 
linic  acid  forms  with  barium  and  calcium  neutral  compounds,  in  which 
the  picropodophyllin  dissolves  by  warming  upon  the  water-bath,  but 
crystallizes  out  after  the  removal  of  these  bases  by  other  acids.  By 
the  continued  action  of  ammonia,  the  picropodophyllin ic  acid  is  par- 
tially decomposed,  becomes  brown  and  insoluble  in  water ;  with  caustic 
alkalies  it  likewise  yields  neutral  compounds,  in  which  the  picropodo- 
phyllin at  first  dissolves,  but  some  time  after  crystallizes  out. 
The  average  of  several  elementary  analyses  gave  for  podophyllotoxin 
carbon  67'62,  hydrogen  7*46  and  oxygen  24*92,  and  for  crystallized 
picropodophyllin,  carbon  67*71,  hydrogen  5*31  and  oxygen  26*98. 
The  analysis  of  picropodophyllotoxin,  of  different  operations,"  gave 
somewhat  varying  results,  which  is  attributed  to  the  difficulty  of  free- 
ing it  from  the  small  amounts  of  adhering  podophyllinic  acid  and 
podophylloquercetin.  The  analysis  of  the  picropodophyllinic  acid 
presents  still  greater  difficulties,  as  it  is  impossible  to  obtain  it  chem- 
ically pure ;  before  the  treatment  with  ammonia  it  always  contains 
traces  of  picropodophyllin,  and  after  the  action  of  ammonia,  which  is 
the  only  method  of  freeing  it  completely  from  picropodophyllin,  it 
contains  again  new  decomposition  ])roducts  which  are  formed  by  the 
action  of  the  former.  The  picropodophyllinic  acid  possesses  further 
no  pharmacological  interest. 
Podophylloquercetin. — This  crystallizes  in  the  form  of  very  short 
needles,  having  a  yellow  color  and  metallic  lustre.  Upon  the  animal 
organism  it  has  neither  emetic  nor  cathartic  properties.  In  the  use  of 
officinal  podophyllin  the  pains  observed  in  the  intestinal  canal  appear 
