104 
Active  Constituents  of  Podophyllin, 
Am.  Jour.  Pharm. 
Mar.,  1882. 
and  crystallizes  from  the  warm  saturated  solutions  upon  cooling ;  it  is 
completely  insoluble  in  water,  oil  of  turpentine  and  petroleum  benzin, 
but  soluble  in  hot  fatty  oils,  from  which,  upon  cooling,  it  gradually 
crystallizes.  Picropodophyllin  is  likewise  soluble  in  glacial  acetic 
acid,  and  crystallizes  therefrom  on  spontaneous  evaporation  in  the 
form  of  large,  cross-like  groups  of  flat  prisms.  By  the  addition  of 
water  to  the  alcoholic  solution  it  is  immediately  precipitated  in  the 
form  of  fine,  long,  silky  needles.  The  taste  of  the  solutions  is 
extremely  bitter,  the  reaction  neutral.  Aqueous  ammonia  does  not 
precipitate  alcoholic  picropodophyllin  solutions,  and  when  such  an 
ammoniacal-alcoholic  solution  is  heated  upon  the  water-bath  until  the 
liquid  portion  has  become  expelled,  the  picropodophyllin  is  converted 
into  a  substance  of  an  acid  reaction,  incapable  of  crystallizing,  and 
without  action  on  the  animal  organism.  The  same  result  is  obtained 
by  heating  the  alcoholic  picropodophyllin  solution,  and  frequently 
adding  portions  of  ammonia  until  the  last  traces  of  crystallization 
disappear,  which  can  easily  be  controlled  by  means  of  the  microscope. 
The  ammonia  must  be  allowed  to  act  for  a  very  long  time,  at  the 
highest  possible  temperature  of  the  water-bath,  and  the  evaporated 
ammonia  must  be  frequently  renewed  by  fresh  additions.  A  few 
grains  of  picropodophyllin  required  for  this  transformation  from  4 
to  6  ounces  of  concentrated  ammonia  water.  Picropodophyllin  dis- 
solves very  readily  in  picropodophyllinic  acid ;  the  behavior  of  these 
solutions  will  be  described  further  on.  Alcoholic  solutions  of  picro- 
podophyllin produce  the  same  effect  when  brought  into  the  -Bnimal 
stomach  as  podophyllin,  although  much  more  active.  For  this  pur- 
pose only  such  solutions  can  be  employed  from  which  it  does  not  sepa- 
rate, and  consequently  hot  solutions  in  dilute  alcohol  or  oil  do  not 
come  into  consideration.  4  centigrams  (0'6  grain),  when  brought  into 
the  stomach  with  the  precautions  required  to  prevent  its  crystallizing 
out,  killed  a  full-grown  cat  after  frequent  vomiting  and  incessant 
mucous  evacuations,  death  occurring  within  from  20  to  24  hours.  6 
centigrams  (0*9  grain)  of  officinal  podophyllin  given  to  a  cat  produced 
simply  evacuation  of  the  bowels  and  vomiting,  but  the  animal  did 
not  die,  and  had  completely  recovered  in  a  few  days.  Picropodophyl- 
lin is  the  more  violent  and  rapid  in  its  action  the  less  it  crystallizes 
out  from  its  solutions  in  the  animal  organism.  On  subcutaneous 
injection  it  crytallizes  in  the  same  spot  in  which  it  is  injected,  and 
produces  absolutely  no  eflPect.    It  is  not  changed  by  acids.    Its  melt- 
