Am.  Jour.  Pharm. 
July.  1903. 
Epinephrin  and  its  Compounds. 
307 
autoclave,  it  not  only  acquired  the  above-named  property,  but  also 
assumed  alkaloidal  characteristics. 
(3)  It  was  also  proved  that  epinephrin  gives  an  iron  compound 
which  is  qualitatively  indistinguishable  from  v.  Flirth's  iron  com- 
pound, and  that  the  iron  compound  made  from  jree  epinephrin  is 
identical  with  that  obtained  from  epinephrin  bisulphate  y  whereas  v. 
Furth  had  maintained  that  only  the  filtrate  from  free  epinephrin 
could  yield  an  iron  compound. 
(4)  In  a  subsequent  paper1  it  was  clearly  proved  that  adrenalin, 
which,  like  suprarenin,  is  devoid  of  alkaloidal  properties,  could  be 
made  to  assume  all  the  alkaloidal  and  other  characteristics  of  epine- 
phrin on  mere  solutions  in  mineral  acids. 
(5)  It  was  further  shown  that  on  benzoating  or  acetylating  the 
iron  compound  of  v.  Furth,  and  on  decomposing  these  derivatives,  a 
series  of  compounds  could  be  prepared  which  are  qualitatively  indis- 
tinguishable from  the  earlier  epinephrin  compounds. 
(6)  In  a  later  paper2  it  was  described  how  the  iron  compound  of 
v.  Furth  was  converted  into  the  acetyl  derivative,  how  this  was  then 
saponified  in  the  autoclave  so  that  a  picrate  and  from  this  in  turn  a 
bisulphate  could  be  prepared,  and  how  this  bisulphate  was  again 
converted  into  the  acetyl  compound.  On  analysis  this  acetyl 
derivative  gave  data  that  agreed  well  with  those  required  lor  the 
triacetyl  derivative  of  an  oxy-epinephrin,  C10HnNO4. 
(7)  In  the  paper  just  alluded  to  it  was  also  shown  that  my  early 
empirical  formula  for  epinephrin,  C17H15N04,.  was  too  large  by  one 
benzoyl  group,  CO  .  C6H5,  and  that  this  was  a  consequence  of  the 
singular  tenacity  with  which  this  lone  radical  defied  all  but  destruc- 
tive methods  for  its  removal  from  the  original  benzoyl  compound. 
On  heating  epinephrin  with  strong  sulphuric  acid,  benzoic  acid  is 
split  off  from  it.  Neither  suprarenin  nor  adrenalin  yield  this  acid 
on  similar  treatment.  Elimination  of  this  retained  radical  from  my 
former  series  of  compounds  and  substitution  of  the  displaced  hydro- 
gen atom  led  to  the  formula  C10HuNO3  as  an  adequate  empirical 
expression  for  epinephrin  with  alkaloidal  properties. 
Without  going  further  into  the  details  of  the  controversy,  it  will 
1  "  On  a  Simple  Method  of  Preparing  Epinephrin  and  Its  Compounds,"  Johns 
Hopkins  Hospital  Bulletin,  Vol.  XIII,  1902. 
2  Johns  Hopkins  Hospital  Bulletin,  November,  1901. 
