320  Epinephrin  and  its  Compounds.  {Am'jJuoiyni903arm' 
of  the  dilute  sulphuric  acid,  and  again  to  subject  it  for  a  couple  of 
hours  to  the  temperature  of  1280  C.  Only  a  small  portion  of  the 
undecomposed  benzoyl  compound  now  remains,  and  a  repetition 
of  the  process  would  still  further  reduce  this  amount. 
From  the  saponified  portions,  it  is  easy  to  prepare  the  picrate, 
bisulphate  and  other  salts  of  monobenzoyl  epinephrin,  C17H17N04. 
That  here,  too,  a  single  benzoyl  radical  is  retained,  just  as  in  the 
earlier  experiments  with  gland  extracts,  is  easily  proved.  One  has 
but  to  prepare  the  bisulphate  and  to  treat  it  with  concentrated  sul- 
phuric acid  with  gentle  heat,  dilute  with  water  and  shake  out  with 
ether  in  order  to  obtain  benzoic  acid  as  proof  that  a  benzoyl  radical 
had  been  retained.  How  many  benzoyl  groups  can  be  taken  up  by 
the  hydrate  C10H13NO3^H2O  has  still  to  be  determined.  It  has 
been  shown  that  alkaloidal  monobenzoyl  epinephrin  can  take  up 
three  additional  acid  radicals,  but  from  this  fact  we  are  not  justified 
in  asserting  that  the  crystalline  hydrate  can  take  up  only  four  acid 
radicals. 
ON  THE  BEHAVIOR  OF  EXTRACTS  OF  THE  GLAND  AND  OF  THE  VARIOUS 
FORMS  OF  THE  BLOOD-PRESSURE-RAISING  PRINCIPLE  TOWARD 
FEHLING'S  SOLUTION. 
In  an  earlier  paper1  I  have  pointed  out  that  while  epinephrin  in  its 
native  state  fails  to  reduce  Fehling's  solution,  the  monobenzoyl  com- 
pounds  and  other  products  prepared  by  me  agreed  with  adrenalin 
in  their  ability  to  reduce  Fehling's  solution.  Certain  preparations 
made  in  accordance  with  processes  first  developed  by  v.  Furth  also 
did  not  in  my  hands  reduce  Fehling's  solution ;  such  were  his  iron 
compound  and  a  very  active  amorphous  and  hygroscopic  sulphate 
or  bisulphate.  In  maintaining  that  native  epinephrin  as  contained  in 
more  or  less  purified  extracts  of  the  suprarenal  gland  does  not  re- 
duce Fehling's  solution,  I  stood  on  common  ground  with  Fraenkel, 
Moore,  Metzger,  and  v.  Furth.  I  have  also  pointed  out,  however, 
that  Brunner2  takes  the  opposite  view ;  that  he  has  stated  positively 
that  an  alcoholic  extract  of  the  gland  does  reduce  Fehling's  solution, 
with  a  resulting  deposition  of  cuprous  oxide .  Aldrich3  has  also  taken 
this  position. 
1  Johns  Hopkins  Hospital  Bulletin,  November,  1901. 
2  Johns  Hopkins  Hospital  Bulletin,  July,  1897. 
3  Am.  Jour.  Physiol.,  Vol.  VII,  p.  359. 
