624 
Dextrococaine. 
Am.  Jour.  Paarm. 
Dec,  1890. 
Dextrococaine  is  prepared  by  heating  the  foregoing  methyl  ether 
with  benzoic  chloride.  It  is  an  oil,  which  gives  a  beautifully  crys- 
talline hydrochloride,  C17H21N04,HC1,  melting  at  205  °,  whereas 
ordinary  cocaine  hydrochloride  melts  at  181-5°.  A  solution  of  1-9 
per  cent,  of  this  salt  in  dilute  alcohol  of  the  same  strength  as 
employed  by  Antrick  (Abstr.,  1887,  506),  in  a  tube  2  dcm.  in  length, 
rotated  the  plane  of  polarization  1-5°  to  the  right.  The  physiologi- 
cal properties  of  dextrococaine  are  similar  to  those  of  cocaine,  but 
its  action  takes  places  more  quickly,  and  is  more  transient. 
The  authors  suggest  that  the  "  methylcocai'ne"  and  "  methylecgo- 
nine,"  prepared  by  C.  Liebermann  and  F.  Giesel  from  mother  liquors 
obtained  in  the  manufacture  of  cocaine,  are  really  dextrococaine  and 
dextroecgonine,  which  are  formed  by  the  action  of  an  alkali  on 
ecgonine  during  the  evaporation  of  the  mother  liquors.  For  the 
better  characterization  of  the  compounds,  a  number  of  new  deriva- 
tives have  been  prepared.  Dextrococaine  is  best  separated  from 
ordinary  cocaine  by  means  of  the  hydrochloride.  The  aurochloride  of 
dextrococaine, C17H21N04,HAuCl4,  is  deposited  from  dilute  alcohol 
in  small,  lustrous,  yellow  crystals  melting  at  149°.  The  platino- 
chloride  is  very  insoluble  in  water  ;  it  crystallizes  from  dilute  alcohol 
in  pale-yellow,  slender  needles  which  melt  at  2 1 8°.  The  hydro- 
bromide  is  obtained  from  hot  water  in  the  form  of  long,  prismatic 
needles.  The  iodide  and  nitrate  crystallize  in  lustrous  leaves ;  both 
they  and  the  sulphate  are  sparingly  soluble  in  water.  Dextro- 
cocaine is  liberated  from  its  salts  by  the  action  of  sodium  hydroxide  ; 
it  is  at  first  obtained  as  an  oily  liquid,  which  readily  solidifies  on 
adding  a  crystal  of  the  substance ;  it  crystallizes  in  prisms  melting 
at  43-45°.  Benzoyl  dextroecgonine  hydrochloride,  C16H19N04HC1, 
is  formed  by  heating  dextrococaine  with  water  for  48  hours ;  the 
solution  is  freed  from  benzoic  acid  by  shaking  with  ether,  and  the 
hydrochloride  precipitated  on  addition  of  hydrochloric  acid ;  it 
crystallizes  from  water  or  alcohol  in  needles,  or  in  short,  broad,  well- 
developed  crystals  melting  at  244-245°.  The  aurochloride  of 
ethyldexlroecgonine,  CnH19N03HAuCl4,  is  deposited  from  dilute  alco- 
hol in  orange-colored  crystals  melting  at  11 5°.  The  correspond- 
ing propyl  compound  has  a  similar  appearance  and  melts  at  1 32°. 
The  isobutyl  compound,  C14H23N03,HAuCl4,  crystallizes  in  orange- 
colored,  transparent  leaves  melting  at  130°.  The  aurochloride  of 
amyldextroecgonine  is  at  first  oily,  after  some  time  it  solidifies  and 
