Am.  Jour.  Pharm.^ 
Jan..  1892.  / 
Strychnine. 
41 
STRYCHNINE.1 
By  J.  Tafel. 
Investigation  has  shown  that  the  compound  named  "  strychnol  " 
by  Loebisch  and  Schoop  (Am.  Jour.  Ph.,  1888,  564),  and  previously 
described  by  the  author  as  strychnine  monhydroxide  (1890),  is  not 
a  phenol,  but  an  imido-acid  of  the  composition  C20H22NO(COOH) : 
NH,4H20;  so  that  it  may  suitably  be  named  strychnic  acid. 
The  substance,  of  the  composition  C21H26N204,  obtained  by  Gal  and 
Etard  (Bull.  Soc.  Chim.y  31,*)8)  by  heating  strychnine  with  a  solu- 
tion of  barium  hydroxide  at  130°,  and  named  by  them  dihydro- 
strychnine,  loses  1  mol.  H20  at  13s0,  and  has,  therefore,  the  com- 
position C21H24N2Os  4-  H20  ;  as  it  is  isomeric  with  strychnic  acid, 
and,  also,  gives  almost  all  the  reactions  of  the  latter,  it  may  be 
termed  isostrychnic  acid.  Both  these  acids  are  formed  when  strych- 
nine is  treated  with  alcoholic  soda  at  100°  or  with  barium  hydroxide 
at  1400,  but  the  relative  quantity  of  the  two  compounds  depends, 
to  a  very  considerable  extent,  on  the  temperature  at  which  the 
reaction  is  carried  out;  when,  for  example,  finely-divided  strychnine 
(10  parts)  is  heated  at  50-550  with  a  solution  of  sodium  (1  part)  in 
alcohol  (10  parts),  strychnic  acid  alone  is  formed  ;  but  if  the  tem- 
perature is  raised  to  70°,  the  product  contains  small  quantities  01 
isostrychnic  acid. 
Strychnic  acid  is  completely  converted  into  strychnine  when  it  is 
heated  at  1900  in  a  stream  of  hydrogen;  its  other  properties  have 
been  already  described  by  Loebisch  and  Schoop.  The  nitrosamine 
hydrochloride,  C20H22NO(COOH):N-NO,HC1  +  H20,  is  obtained 
when  the  acid  is  treated  with  sodium  nitrite  and  hydrochloric  acid 
in  the  cold ;  it  crystallizes  from  alcohol  in  yellowish  prisms,  is 
moderately  easily  soluble  in  cold  water,  and  gives  the  nitroso- 
reaction ;  on  reduction  with  zinc-dust  and  acetic  acid,  it  is  converted 
into  a  compound  which  reduces  Fehling's  solution,  but  when 
warmed  with  tin  and  hydrochloric  acid  it  yields  strychnic  acid 
hydrochloride. 
Strychnic  acid  methiodide,  C21H24N203MeI  -j-  H20,  is  formed  when 
an  aqueous  solution  of  the  sodium  salt  of  strychnic  acid  methiodide 
is  acidified  with  dilute  acetic  acid,  and  also  when  methylstrychnine 
is  treated  with  cold  hydriodic  acid;  it  loses  its  water  at  120-130°, 
1  Annalen,  264,  33-84  ;  Jour.  Chem.  Soc,  1891,  p.  1262. 
