528 
Adrenalin. 
( Am.  Jour.  Pharm. 
(  November,  1901. 
T.  B.  Aldrich,  of  Detroit,  reported  in  his  paper  (August  number 
of  the  American  Journal  of  Physiology)  that  he  had  also  succeeded 
in  the  isolation  of  the  crystalline  active  principle  of  the  suprarenal 
glands  by  the  use  of  basic  acetate  of  lead  as  a  precipitant,  and  later 
by  ammonia.  He  proved  by  analysis  that  his  substance  was  exactly 
identical  with  my  adrenalin. 
Aldrich's  formula  is  C9H13N03.  which  differs  with  mine  by  less 
CH2.  Aldrich  observes  that  "  if  we  subtract  a  benzoyl  residue 
C7HsO  from  Abel's  formula  for  epinephrin  (C17H15N04)  we  obtain 
C10H10NO3,"  which  is  not  very  far  from  Aldrich's  own  result. 
It  will  be  of  some  interest  to  arrange  tabularly  the  empirical 
formulas  of  the  glandular  active  principle,  according  to  the  results 
and  claims  by  different  authors  : 
Furth.  Abel.  Aldrich.  Takamine. 
C5H7N02  C17H15N04  C9H13N03  C10H15TO3 
or 
C5H9N02. 
The  further  investigations  on  different  chemical  behaviors  of 
adrenalin  will  help  to  determine  the  correct  formula  for  this  inter- 
esting product. 
Salts  :  Adrenalin  is  very  soluble  in  acids  and  alkalies,  and  forms 
its  salts  which  are  not  crystallizable.  I  made  three  kinds  of  salts — 
hydrochloride,  sulphate  and  benzoate — by  carefully  dissolving  adren- 
alin with  the  acids  respectively  and  evaporating  in  vacuo  over  strong 
sulphuric  acid.  In  the  long  course  of  time  they  all  became  dark 
brown,  brittle  masses,  deliquescent  in  the  air.  So  far  my  efforts  to 
crystallize  them  have  failed. 
Alkali  compounds  are  easily  affected  by  oxygen  of  air  and  their 
crystallization  is  entirely  impossible. 
Benzoyl  Compounds :  Pure  adrenalin  is  dissolved  in  a  slight  ex- 
cess of  an  alkali  solution,  in  a  separating  funnel,  and  benzoyl 
chloride  is  gradually  added,  shaking  the  contents  briskly  after  each 
addition.  After  shaking  a  quarter  or  half  an  hour  a  yellow-brownish 
oily  liquid  will  settle  on  the  bottom  of  the  funnel,  and  supernatant 
liquid  will  be  found  suspending  some  crystalline  substance,  and 
reacts  no  longer  with  ferric  chloride,  after  acidulating  with  hydro- 
chloric acid,  showing  that  adrenalin  has  entirely  combined  with 
benzoyl  by  the  manipulation.  The  oily  liquid  is  first  washed  with 
water,  and  then  with  a  diluted  sodium  carbonate  solution,  followed 
