Am.  Jour.  Pharm.1 
July,  1903.  J 
EpinepJirin  and  its  Compounds. 
323 
earths ;  that  is,  that  on  the  addition  of  any  of  these  to  either  modifi- 
cation of  our  substance,  a  volatile  base  of  a  coniin-piperidin-like 
odor  is  liberated,  and  in  the  course  of  time  a  pigment  which  I  have 
named  epinephrinic  acid  is  also  formed.  This  pigment  I  assume  to 
be  the  oxidation  product  of  the  pyrocatechin-like  part  of  the  mole- 
cule. It  was  shown  in  my  earliest  papers  that  pyrocatechin  cannot 
be  split  off  from  epinephrin  by  boiling  with  mineral  acids  of  ordi- 
nary strength.  In  a  later  paper  it  was  mentioned  that  when  mono- 
benzoyl  epinephrin  bisulphate  is  heated  in  a  sealed  tube  with  25 
per  cent,  hydrochloric  acid  to  1500  C,  a  small  amount  of  an  ether- 
soluble  substance  is  obtained  which  gives  a  fine  green  color  on  the 
addition  of  ferric  chloride.  V.  Fiirth  has  also  found  that  on'dry  dis- 
tillation a  substance  soluble  in  ether  is  obtained  which  behaves 
toward  ferric  chloride  like  pyrocatechin.  Takamine1  has  obtained 
similar  products  by  fusing  adrenalin  with  caustic  potash,  but  makes 
no  reference  to  these  earlier  observations.  From  these  observations 
it  seems  fair  to  conclude  that  there  exists  a  residue  C6H3(OH)2 — or 
C6H2(OH)3  in  the  molecule  of  our  substance.  I  had  already  ex- 
pressed this  opinion  in  my  preliminary  constitutional  formula2  for 
monobenzoyl  epinephrin,  C17H17N04,  and  it  may  be  remarked  that 
the  subsequent  discovery  of  an  unremoved  benzoyl  group,  C6H5CO, 
in  this  form  of  epinephrin  does  not  invalidate  the  position  taken  by 
me  at  that  time  in  respect  to  the  pyrocatechin-like  residue  of  the 
molecule. 
Acting  on  the  supposition  that  the  molecule  of  the  blood-pressure- 
raising  principle  consists  of  two  cyclic  compounds,  one  a  hydroxy- 
lated  benzene  nucleus,  the  other  a  pyrrol-like  base,  I  have  lately 
undertaken  a  study  of  the  action  of  nitric  acid  on  both  epinephrin, 
C10H13NO3,  and  its  hydrate. 
Results  thus  far  obtained  indicate  that  the  products  of  this  oxida- 
tion are  identical  in  the  two  cases.  The  following  example  will 
illustrate  the  process :  In  very  small  portions  at  a  time,  10  grammes 
of  the  purified  hydrate  is  dissolved  in  60  c.c.  of  nitric  acid,  of 
sp.  gr.  1-2,  in  a  platinum  bowl  on  the  water-bath.  The  oxidation 
goes  on  with  considerable  violence,  and  care  must  be  taken  to  avoid 
loss  of  material  in  consequence  of  foaming.     When  the  evolution  of 
1  Am.  Jour.  Pharmacy,  Vol.  73,  1901,  page  529. 
2See  Zeitschr.f.  Physiol.  Chem.,  Bd.  XXVIII,  page  347. 
