456 
Mydriatic  Alkaloids. 
J  Am.  Jour.  Pharm 
I     October,  1903. 
Thanks  to  investigations  which  have  been  completed  during  the 
past  year  both  in  Europe  and  America,  there  is  now  absolute  proof 
that  the  alkaloids  atropine  and  hyoscyamine  are  stereo-isomers  and 
that  the  former  is  the  racemic  form  of  the  latter. 
Ladenburg  long  ago  proved  that  these  two  alkaloids  are  isomers 
with  the  formula  C17H23N03.  The  optical  activity  of  hyoscyamine 
was  recognized  by  a  number  of  investigators  at  about  the  same  time, 
but  the  exact  rotation,  (a)D  =  —  21 -8°,  was  first  determined  by  Laden- 
burg.  In  the  case  of  atropine  there  was  much  discussion  regarding 
its  behavior  toward  polarized  light,  owing  to  the  difficulty  of  isolat- 
ing it  in  a  perfectly  pure  state.  Not  until  within  comparatively 
recent  years  has  the  optical  inactivity  of  atropine  been  universally 
accepted  as  a  fact. 
In  an  elaborate  series  of  researches  upon  the  constitution  of  these 
alkaloids  Ladenburg  showed  that  they  were  both  tropic  acid  esters 
of  the  base  tropine,  /.  e.,  he  succeeded  in  splitting  them  both  into 
tropine  and  tropic  acid  by  means  of  saponification.  This,  together 
with  the  well-known  fact  that  hyoscyamine  is  most  easily  converted 
into  atropine,  led  to  the  conclusion  that  atropine  is  the  racemic  form 
of  hyoscyamine,  though  some  proofs  were  still  wanting.  This,  of 
course,  implies  the  existence  of  the  complement  of  ordinary  or 
1-hyoscyamine,  viz.,  d-hyoscyamine,  but  this  had  never  been  isolated 
or  prepared.  Ladenburg  made  many  attempts  to  resolve  atropine  into 
its  optically  active  components  along  the  line  of  Pasteur's  work,  but 
only  partially  succeeded,  inasmuch  as  he  obtained  what  he  called  a 
right  atropine,  which  must  have  been,  in  the  light  of  our  recent  knowl- 
edge, a  mixture  of  atropine  and  ,d-hyoscyamine.  Up  to  six  months 
ago  there  was  no  evidence  in  literature  of  the  existence  of  such  a 
compound  as  d-hyoscyamine. 
It  was  at  this  time  that  an  interesting  and  important  pharmaco- 
logical investigation  bearing  directly  upon  this  subject  was  being 
pursued  by  Dr.  Cushny,  of  the  University  of  Michigan.  Clinical  and 
laboratory  reports  upon  the  action  of  these  two  bases  in  the  body 
are  not  wanting,  but  tney  are  so  conflicting  and  so  widely  at 
variance  with  each  other  that  no  reliance  can  be  placed  upon  them. 
Some  reported  hyoscyamine  as  inert,  others  that  its  action  is 
identical  with  atropine,  while  still  others  claim  that  their  actions 
are  widely  different.  It  is  very  evident  that  some  of  these  oper- 
ators were  working  either  upon  mixtures  of  alkaloids  or  with 
