194 
a-  and  ft-Encaine. 
Am.  Jonr.  Pharm. 
April,  1902. 
THE  IDENTIFICATION  AND  PROPERTIES  OF  a-  AND 
/9-EUCAINE.1 
By  Charles  Lathrop  Parsons. 
Two  new  alkaloids  under  the  names  a-eucaine  and  ^9-eucaine  have 
recently  been  offered  to  the  medical  and  dental  profession  for  use 
as  a  local  anesthetic.  There  is  scarcely  a  reference  to  either  in 
any  strictly  chemical  journal,  but  their  use  and  physiological  prop- 
erties have  been  very  fully  discussed  in  medical  and  pharmaceutical 
publications.  Although  they  are  proprietary  drugs,  the  fact  that 
/9-eucaine  is  so  often  substituted  for  cocaine,  in  dental  preparations, 
hay-fever  remedies,  and  other  proprietary  medicine,  makes  it  highly 
desirable  that  their  distinctive  properties  be  carefully  studied  and 
that  methods  be  found  for  their  identification  and  separation  from 
cocaine  and  other  alkaloids.  It  was  owing  to  the  fact  that  I  was 
called  upon  to  analyze  a  special  dental  preparation  containing 
cocaine  that  my  attention  was  first  called  to  the  existence  of  the 
alkaloid,  and  I  was  greatly  handicapped  by  the  silence  of  chemical 
literature  upon  the  subject. 
«-Eucaine  was  first  obtained  by  George  Merling2  by  synthesis 
from  triacetonamine  through  triacetonamincyanhydrin  to  triace- 
tonalkamincarbonic  acid,  which,  by  the  action  of  benzoyl  chloride 
and  subsequent  action  of  methyl  iodide  in  caustic  potash  solution, 
becomes  w-methylbenzoyltetramethyl-^-oxypiperidincarbonic  acid 
methylester  or  "  a-eucaine."  This,  when  treated  with  hydrochloric 
acid,  acts  like  other  alkaloids  forming  a  hydrochloride,  in  which 
form  it  is  prepared  and  sold. 
^-Eucaine  was  discovered  by  Albrecht  Schmidt  and  George  Mer- 
ling8 and  was  obtained  by  purifying  the  vinyldiacetonalkamine  of 
Fischer4  and  substituting  a  benzoyl  group  for  the  hydrogen  atom  of 
the  hydroxyl.  Thus  "/?-eucaine  "  or  benzoylvinyldiacetonalkamine, 
is  also  an  alkaloid  which,  when  treated  with  hydrochloric  acid, 
forms  the  hydrochloride. 
It  will  be  seen  from  the  structural  formulas  of  a-  and  /?-eucaine 
that  they  have  a  close  relation  to  cocaine  and  to  tropacocaine.  It 
1  Read  at  the  Denver  meeting  of  the  American  Chemical  Society,  August 
29,  1901,  and  reprinted  from  the  Jour.  Amer.  Chem.  Soc,  1901,  p.  885. 
s  Apoth.  Ztg.  (1896),  p.  293,  418,  448. 
3  Virchow'8  Archives  /.path.  Anat.  und  Phys.  (1896,)  vol.  145. 
4  Ber.  d.  chem  Ges.,  17,  1894. 
