324 
Epinephrin  and  its  Compounds. 
Am.  Jour.  Pharm. 
July,  1903. 
gases  has  largely  subsided,  10  c.c.  of  fuming  nitric  acid  is  added 
and  the  whole  is  then  concentrated  on  the  water-bath,  water  being 
added  from  time  to  time  as  the  mass  begins  to  thicken.  After  the 
removal  of  excess  of  acid  and  cooling,  the  contents  of  the  dish  are 
found  to  be  crystalline  and  odorless. 
The  larger  part  of  this  crystalline  mass  consists  of  oxalic  acid. 
The  barium,  lead,  sodium  and  calcium  salts  of  this  acid  were  pre- 
pared, as  also  its  diethyl  ester.  The  calcium  salt  CaC204  .  H20,  as 
prepared  from  a  hot  concentrated  solution  of  the  sodium  salt,  was 
found  to  contain  27-39  per  cent.  Ca,  the  theoretical  amount  of  cal- 
cium for  CaC204  .  H20  as  thus  prepared.  The  tetragonal  crystals, 
CaC204 .  3H20,  were  also  prepared  from  the  sodium  salt  and  the  free 
acid  was  oxidized  with  potassium  permanganate,  and  in  other  ways 
was  shown  to  have  all  the  properties  of  oxalic  acid. 
The  other  chief  product  of  the  above  oxidation  consists  of  a  salt 
(oxalate  ?)  of  the  unknown  nitrogenous  base  which  I  have  called  the 
coniin-piperidin-like  body  on  account  of  its  peculiar  offensive  and 
penetrating  odor.  The  addition  of  an  alkali  to  these  crystals 
immediately  liberates  this  odor.  It  is  evident,  then,  that  this  part 
of  the  molecule  has  withstood  the  very  energetic  treatment  with 
nitric  acid  above  described.  Further  treatment  with  iodine  trichlo- 
ride does  not  destroy  this  base,  but  enables  one  to  obtain  it  as  a 
salt  crystallizing  in  slender  prisms,  very  soluble  in  water  and  alcohol 
and  but  little  soluble  in  ether.  A  diazo-compound  of  these  crystals 
has  also  been  formed. 
In  its  general  behavior  toward  destructive  chemicals,  as,  for  exam- 
ple, on  fusion  with  powdered  potassium  hydrate,  this  salt  reminds 
one  forcibly  of  the  behavior  of  certain  pyrrol  derivatives  under  simi- 
lar circumstances.  When  thus  treated  an  odor  like  that  of  pyrrolidin 
arises ;  later,  as  the  fusion  continues,  this  gives  place  to  the  fishy 
odor  of  amines,  and  this  in  turn  gives  place  to  that  of  pyrrol,  as 
proved  by  the  pine  sliver  reaction.  Analyses  of  this  specific  part 
of  the  molecule  of  epinephrin  and  adrenalin  will  soon  be  published. 
It  is  evident  from  the  above  that  the  pyrocatechin-like  part  of  the 
molecule,  which  in  some  measure  resists  the  destructive  action  of 
acids  in  sealed  tubes  and  of  fusion  with  alkalies,  is  oxidized  by  nitric 
acid  to  oxalic  acid  and  simpler  products,  while  the  nitrogenous  part 
of  the  molecule  remains,  in  large  part  at  least,  entirely  unaffected  by 
this  oxidation.     Researches  now  in  progress  will,  it  is  hoped,  soon 
