34Q 
Chemical  Notes. 
i  Am.  Jour.  Pharm. 
t        July.  1890. 
On  Damascenine,  an  Alkaloid  from  Nigella  damascena  L.  Dr. 
A.  Schneider  {Pharm.  Centralh.,  1890,  p.  174  and  191)  has  isolated 
the  fluorescent  principle  from  the  seeds  of  the  above  plant  and 
shows  it  to  be  an  alkaloid  present  to  the  amount  of  o  1  per  cent.^ 
and  localized  in  the  testa.  The  crushed  seeds  were  macerated  with 
benzin  and  expressed,  this  being  repeated  a  number  of  times. 
This  solution  was  then  treated  three  times  with  dilute  hydrochloric 
acid  (1  pt.  H  CI  Ph.  Germ.,  3  pts.  H20)  filtered  and  made  alkaline 
with  sodium  carbonate  solution.  In  the  first  portion  this  caused  a 
precipitate,  the  remaining  portions  as  well  as  the  filtrate  from  the 
first  were  extracted  with  chloroform.  This  solution  was  extracted 
with  acid  of  the  above  strength  and  the  alkaloid  precipitated  with 
solution  of  sodium  carbonate.  The  precipitate  which,  however,  was 
not  solid  but  consisted  of  small  oily  drops  was  dissolved  in  absolute 
alcohol,  and  this  solvent  evaporated  over  sulphuric  acid  in  a  vacuum 
desiccator.  The  oil  obtained  was  crystallized  in  a  freezing  mixture, 
and  the  cold  solid  pressed  between  bibulous  paper.  Thus  prepared, 
the  alkaloid  melts  at  270  C,  and  boils  at  1680  C,  although  it  is 
volatile  at  ordinary  temperature.  The  sp.  gr.  of  the  melted 
damascenine  is  roi.  The  alkaloid  is  insoluble  in  cold  water  and 
slightly  so  in  hot,  easily  in  ethyl  and  methyl  alcohols,  chloroform, 
methyiodide,  carbon  bisulphide,  benzin,  petroleum  ether,  benzol, 
fatty  oils  and  paraffine.  All  solutions  of  the  free  alkaloid  show  blue 
fluorescence.  Precipitates,  consisting  of  minute  oily  drops,  are 
formed  with  ammonia,  sodium  hydrate  and  carbonate,  corrosive  sub- 
limate (all  white),  iodopotassium  iodide  (brownish-purple,  gradually 
crystallizing),  potassio-mercuric  iodide  (Mayer's  reagent  white  crys- 
tallizing, on  rubbing),  potassio-cadmic  iodide  and  phosphomolybdic 
acid  (both  white,  gradually  turning  yellow),  potassio-bismuthic  iodide 
(brown,  gradually  crystallizing),  Nessler's  reagent  (grayish-brown), 
platinum,  palladium  and  gold  chlorides  (crystalline,  the  Au  salt  soon 
blackens  by  reduction),  picric  acid  and  potassium  bichromate  (yellow, 
crystalline).  The  characteristic  color  reaction  is  obtained  by  melt- 
ing the  nitrate  which  turns  blue.  A  solution  of  a  salt  with  sulphuric 
acid  and  potassium  bichromate  turns  blood  red  or  violet  red.  Solu- 
tions of  the  alkaloid  containing  an  excess  of  nitric  acid  soon  turn 
violet  red,  which  color  is  soluble  in  alcohol,  chloroform  and  acetic 
acid,  and  has  almost  the  same  color  as  methyl  violet.  The  chloride 
melts  at  1210  C,  the  nitrate  at  980  C.  (at  1800  C.  blue,  at  2  10° 
