3i6 
Epinephrin  and  its  Compounds. 
Am.  Jour.  Pharm. 
July,  1903. 
I  have  thus  far  found  solution  in  strong  sulphuric  acid  to  be  the 
best  means  of  effecting  the  dehydration.  For  example,  2*2  grammes 
of  the  pure  crystalline  hydrate  analyzed  above  was  dissolved  in 
small  portions  at  a  time  in  5  to  7  c.c.  of  sulphuric  acid  (prepared  by 
adding  I  y2  c.c.  of  water  to  16  c.c.  of  concentrated  sulphuric  acid), 
the  process  being  a  tedious  one  requiring  several  hours.  After  the 
solution  has  been  effected  it  may  be  allowed  to  stand  over  night  in 
the  desiccator.  The  sulphuric  acid  solution  is  then  dropped  slowly 
into  absolute  alcohol,  being  stirred  all  the  time. 
A  white  precipitate  immediately  falls  out,  which  may  be  further 
increased  by  the  addition  of  a  little  ether. 
After  collecting  the  sulphate  thus  precipitated  on  the  filter  and 
washing  it  with  absolute  alcohol  and  ether,  it  is  quickly  dried  in 
vacuo. 
As  thus  thrown  out  in  the  amorphous  form,  this  sulphate  natu- 
rally retains  some  adherent  sulphuric  acid,  which  may,  however,  be 
removed  with  the  greatest  ease  by  dissolving  it  in  a  little  water  and 
dropping  its  aqueous  solution  into  absolute  alcohol  under  constant 
stirring.  After  being  washed  with  alcohol  and  ether  and  dried  in 
vacuo  over  sulphuric  acid,  this  sulphate  constitutes  an  almost 
white  or  grayish-white  non-hygroscopic  product,  indistinguishable 
in  appearance  from  the  monobenzoyl  sulphate  of  my  earlier  papers. 
It  dissolves  very  easily  in  water,  dilute  solutions  being  colorless, 
while  very  concentrated  solutions  take  on  a  greenish-black  color. 
Concentrated  solutions  of  the  hydrate  (C10H18NO3^H2O)  in  dilute 
acids  take  on  a  dark-brown  color,  while  dilute  solutions,  I  to  100  or 
1  to  1,000,  are  also  colorless. 
No  permanent  salts  of  the  crystalline  hydrate  have  thus  far  been 
made.  Takamine,  for  example,  in  attempting  to  make  salts  of  the 
hydrate  (adrenalin)  obtained  only  noncrystallizable  "  brown  brittle 
masses  deliquescent  in  the  air."  The  above  dehydration,  however, 
at  once  gives  us  a  method  for  obtaining  a  whole  series  of  permanent 
non-hygroscopic  salts.  There  is  every  indication,  too,  that  these  can 
be  obtained  in  the  crystalline  form.  This  sulphate,  when  thrown 
out  of  very  dilute  solutions  in  weak  alcohol  with  ether,  is  deposited 
in  microcrystalline  form  on  the  sides  of  the  vessel.  The  picrate  also 
has  been  obtained  by  me  in  the  form  of  nodules  made  up  of  smal 
prisms,  though  not  always  perfectly  formed. 
This  sulphate  of  alkaloidal  properties  thus  prepared  appears,  as 
