360 
Andromedotoxin. 
Am.  Jour.  Pharm. 
July,  1889. 
ANDROMEDOTOXIN.1 
By  P.  C.  Plugge  and  H.  G.  de  Zaayer. 
Plugge  first  obtained  andromedotoxin,  which  he  extracted  from 
Andromeda  japonica,  A.  polifolia,  A.  Catesbcei  and  A.  calyculata  (see 
Am.  Jour.  Phar.,  1883,  196). 
The  aqueous  extract  of  Rhododendron  ponticum  leaves  was  treated 
successively  with  normal  and  basic  lead  acetate.  From  the  filtrate, 
the  lead  was  separated  by  hydrogen  sulphide,  and  the  liquid  was  con- 
centrated by  slow  evaporation  in  the  air,  and  treated  repeatedly  with 
considerable  quantities  of  chloroform.  The  residue  left  on  evaporat- 
ing the  chloroform  was  purified  by  re-solution  in  chloroform  (or  alco- 
hol) and  precipitation  by  the  addition  of  a  considerable  amount  of 
ether.  This  treatment  several  times  repeated  finally  yielded  well- 
formed,  crystalline  needles  which  melted  at  228-229°.  At  12.5°, 
water  dissolves  2  81  per  cent. ;  alcohol  (of  94  per  cent.)  11*1 ;  amyl 
alcohol,  1-14;  chloroform,  0'26;  ether,  0'07 ;  benzene,  0*004.  The 
solutions  in  water,  alcohol,  and  amyl  alcohol  are  lsevorotatory,  whilst 
that  in  chloroform  is  dextrorotatory.  Andromedotoxin,  C31H51O10,  is 
an  indifferent  non-nitrogenous  compound  ;  its  solution  in  different  li- 
quids has  a  neutral  reaction,  and  it  is  not  precipitated  by  any  of  the 
so-called  general  alkaloid  reagents.  Its  reaction  with  dilute  and  con- 
centrated mineral  acids  is  characteristic,  as  with  them  it  gives  in- 
tensely red  decomposition-products.  Concentrated  sulphuric  acid 
gives  a  dark  reddish-brown,  which  becomes  deeper  red  on  warming, 
and  turns  light  mulberry-red  on  dilution  with  water.  The  addition 
of  alkali  removes  the  color,  which  reappears  on  acidifying.  Evapo- 
ration with  dilute  (1:5)  sulphuric  acid  gives  a  beautiful  rose-red 
color.  The  pure  material  gives  off  no  odor  during  this  evaporation, 
but  if  not  completely  purified,  a  strong  and  very  characteristic  odor  of 
ericinol  is  evolved.  Evaporation  with  dilute  hydrochloric  acid  gives 
a  residue  somewhat  more  violet-red  in  tint.  Evaporation  with  phos- 
phoric acid  gives  a  mulberry-red  residue,  clearly  perceptible  with  very 
minute  quantities,  as  in  the  case  of  the  other  acids.  The  fatal  dose  for 
small  animals  has  been  found  to  vary  from  0'l-0'45  mgrm.  per  kilo, 
body-weight.  No  chemical  antidote  is  known  as  yet.  In  investigat- 
ing poisoning  cases,  DragendorfPs  process  is  recommended ;  but  no 
acid  should  be  used  for  extraction,  as  the  solubility  of  the  poison  is 
1  (Arch.  Pharm.  [3],  xxvi.,  9y7-998 :  reprinted  from  Jour.  Chem.  Soc,  March 
1889,  p  278). 
