Am.  Jcmr.  Pharm. 
April,  1911. 
} 
Active  Principle  of  Ergot. 
165 
lethylamin,  phenylethylamin  and  isoamylamin  to  be  present  in  ergot. 
Para-oxyphenylethylamin  can  be  shaken  from  water  into  ether  pro- 
vided sodium  carbonate  is  used,  but  not  by  means  of  NaOH'.  Barger 
and  Dale  freed  it  as  a  benzoyl  compound.  The  rise  in  blood 
pressure  following  the  injection  of  ergot  preparations  was  almost 
entirely  due  to  the  first  constituent;  the  other  two  played  only  a 
subordinate  role  in  the  activity  of  ergot.  They  believed  the  first 
to  be  derived  from  tyrosin,  while  the  others  were  traced  to  leucin 
and  phenylalanin,  respectively.  Para-hydroxyphenylethylamin  pro- 
duces a  rise  in  blood  pressure  much  like  adrenalin,  only  weaker. 
This  similarity  in  action  might  be  expected  from  the  close  chemical 
relationship  with  adrenalin,  which  may  be  represented  as 
Unlike  adrenalin,  this  body  is  active  when  administered  by  mouth 
and  produces  no  glycosuria.  Isoamylamin  and  phenylethylamin 
have  a  similar  action  but  less  marked.  Both  compounds  exert 
qualitatively  the  same  kind  of  action  on  the  true  sympathetic 
system  as  adrenalin.  Dale  and  Dixon  say  that  "  Both  p.  hydroxy- 
phenylamin  and  isoamylamin  were  found  to  cause  contractions 
of  the  uterus  and  vagina  of  the  rabbit  in  all  functional  conditions," 
and  the  injection  of  either  base  would  bring  on  labor  in  pregnant 
animals.  Like  adrenalin,  p.  oxyphenylethylamin  causes  inhibition 
in  the  non-pregnant  uterus  of  the  cat,  and  causes  contraction  in 
the  pregnant  uterus,  however,  it  is  much  less  toxic. 
Kehrer  noted  that  certain  extracts  of  ergot  produced  an  intense 
activity  on  the  non-pregnant  uterus  of  the  cat,  and  that  it  was 
the  dialyzed  ergotin  of  Wernich  which  especially  showed  this 
action.  This  preparation  is  made  by  a  slow  process  of  dialysis, 
which  suggested  that  it  was  due  to  the  action  of  micro-organisms. 
The  evidence  at  present  points  to  ^-iminazoylethylamine  as  the 
compound  to  which  this  action  is  to  be  traced.  This  compound  is 
derived  from  histidine  by  the  elimination  of  carbon  dioxide,  in  the 
same  manner  as  p-hydroxyphenylethylamin  is  derived  from  tyrosine. 
Thus  histidine 
HO 
H0< 
>CH(OH)CH2NHCH3. 
CH-NH 
\ 
CH-NH 
Vh+co, 
.CH 
II 
c 
CH^.CH.-NHj 
