Am.  Jour.  Pharm.  ) 
July,  1913.  / 
Current  Literature. 
331 
.(a.)  Cytisoline,  CnHuON,  a  feebly  basic,  crystalline  solid,  melting  when 
pure  at  1980. 
(b)  /3-Cytisolidine,  G1H15N,  a  basic  oil,  yielding  a  crystalline  picrate 
(m.p.  2290)  and  platinichloride  (m.p.  2340). 
(c)  A  mixture  of  hydrocarbons  melting  at  185-2300. 
(d)  Ammonia. 
Later  Freund  found  that  on  electrolytic  reduction,  cytisine  was 
changed  into  a  base,  tetrahydrodeoxycytisine.  The  action  of  hy- 
driodic  acid  seemed  to  offer  the  only  hope  for  determining  the 
constitution  of  cytisine.  Many  attempts  were  made  to  get  some 
product  of  oxidation  from  the  alkaloid  which  might  throw  some 
light  on  the  problem  of  its  constitution.  It  is  readily  attacked 
by  oxidizing  agents;  such  as  potassium  permanganate  and  chromic 
acid,  but,  however  the  conditions  are  varied,  no  pure  product  can 
be  isolated  except  oxalic  acid.  Attempts  to  decompose  cytisine 
by  the  action  of  acids  or  alkalies  at  high  temperature  proved 
unavailing.  Cytisine  is  stable  to  a  remarkable  degree  towards 
these  reagents.  The  experiments  of  Freund  were  very  carefully 
repeated  by  Ewins,  who  gives  in  detail  his  work  on  the  subject 
and  seems  to  think  that  the  constitution  of  this  alkaloid  remains 
an  open  question  (A.  J.  Ewins,  B.Sc.  Transactions  of  the 
Chemical  Society,  Vol.  103,  1913.  London.) 
John  K.  Thum. 
THE  CONSTITUTION  AND  SYNTHESIS  OF  DAMASCENINE,  THE  ALKALOID 
OF  NIGELLA  DAMASCENA. 
The  literature  relating  to  this  alkaloid  is  briefly  reviewed  and 
the  main  facts  brought  out.  Schneider  (Pharm.  Centr.-h.,  1890, 
31,  173)  was  the  first  to  isolate  it  from  the  seeds  of  Nigella  da- 
mascena.  He  described  it  as  a  crystalline  solid,  m.  p.  270,  with  the 
composition  C10H15O3N.  Subsequently  this  was  shown  to  be  sub- 
stantially correct,  the  formula  really  being  C10H13O3N. 
The  constitution  of  damasceninic  acid,  easily  formed  from 
damascenine,  was  shown  by  Keller  to  be  2-methylamino-3~ 
methoxybenzoic  acid.    He  unsuccessfully  attempted  its  synthesis. 
Ewins  gives  his  method  of  extracting  the  alkaloid  from  the  seeds 
by  the  shaking  out  process,  using  light  petroleum.  The  alkaloid 
and  its  salts  agreed  absolutely  with  the  synthetic  product  and  its 
salts. 
