Am.  Jour.  Pharm.  \ 
July,  1903.  J 
Epinephrin  and  its  Compounds. 
305 
(6)  The  addition  of  an  alkali,  as  sodium  hydrate,  to  the  free  base 
or  one  of  its  salts  produces  two  substances,  one  of  which  is  a  basic 
body  of  a  peculiarly  intense  and  nauseating  odor,  reminding  one  of 
a  mixture  of  coniin  and  piperidin ;  the  other,  a  dark  pigment  of  an 
acid  character.  This  latter  decomposition  product  was  called  epine- 
phrine acid. 
(7)  On  smelting  epinephrin  with  powdered  alkalies,  a  small  quan- 
tity was  obtained  of  a  substance  that  corresponded  in  its  reactions 
to  skatol.  Dry  distillation  with  zinc  dust  in  a  current  of  dry  hydro- 
gen yielded  amines,  benzaldehyde,  and  pyrrol.  On  heating  epinephrin 
bisulphate  in  a  sealed  tube  with  25  per  cent,  hydrochloric  acid  to 
1500  C,  a  small  amount  of  an  ether-soluble  substance  was  obtained 
which  took  on  a  green  color  on  the  addition  of  ferric  chloride.  No 
attempt  was,  however,  made  to  identify  this  body  with  pyrocatechin 
or  pyrocatechinic  acid.  An  acid  with  a  melting  point  of  120°  C.  and 
all  the  properties  of  benzoic  acid  was  also  obtained  by  this  treatment. 
In  consequence  of  these  reactions,  epinephrin  was  declared  to  belong 
in  a  general  way  to  the  class  of  pyrrol  derivatives. 
The  Work  of  von  Fiirth.- — Shortly  after  the  appearance  of  the 
paper  by  Abel  and  Crawford,  v.  Fiirth  entered  the  field.  On 
the  basis  of  a  series  of  analyses  of  an  impure  acetyl  product 
prepared  directly  from  crude  extracts  of  the  gland,  this  writer1 
assumed  the  blood-pressure-raising  constituent  to  be  either  tetrahy- 
drodioxypyridin,  C5H9N02,  or  dihydrodioxypyridin,  C5H7N02.  No 
more  need  be  said  in  reference  to  this  claim  since  v.  Fiirth 2  has 
himself  lately  abandoned  this^heory.  He  has,  however,  made  some 
contributions  of  value,  notably  the  isolation  of  the  blood-pressure- 
raising  principle  in  the  form  of  a  physiologically  active,  though  im- 
pure, iron  compound.  This  compound  is,  however,  so  difficult  to 
purify  that  its  analysis  throws  but  little  light  on  the  true  elementary 
composition  of  our  substance.  V.  Fiirth  furnished  no  analyses  in 
connection  with  his  earlier  work  on  this  iron  compound.  In  those 
furnished  later,  he  assumes  by  comparison  with  the  commercial 
preparation,  adrenalin,  that  those  fractions  of  his  iron  compound 
which  show  the  highest  percentage  of  carbon  most  nearly  represent 
1  Zeitschr.  f.  physiol.  Chem.,  Bd.  XXIV,  page  142;  XXVI,  page  15;  XXIX, 
page  105. 
Beitrage  zur  chem.,  Physiol,  u.  Pathol.,  Bd.  I,  page  243. 
