HARMALINE. 451 



on the addition of sulphuric acid. From this salt the 

 hase can be set free by means of baryta, but it remains 

 dissolved, imparting to the solution a deep yellow 

 color ; and on evaporating, it is decomposed. 



On boiling its salts with potassium or barium hy- 

 droxide, sinapine is decomposed, yielding choline (p. 140) 

 and sinapic acid (p. 381). 



13. Harmaline. 



Occurrence. In the seeds of Peganum harmahi (a 

 plant growing on the steppes of Russia). 



Preparation. The powdered seeds are exhausted 

 with water containing a little sulphuric or acetic 

 acid. The alkaloid is precipitated from the extract 

 with a concentrated solution of sodium chloride, in 

 the form of the hydrochlorate ; and this, after being 

 purified by recrystallization, decomposed with ammo- 

 nia. 



Properties. Colorless, rhombic octahedrons; spar- 

 ingly soluble in water and cold alcohol, more easily in 

 hot alcohol ; fuses when heated. Combines with acids, 

 forming yellow salts, which are for the greater part 

 easily soluble. Monatomic base. 



Harmine, C 13 H 12 K 2 0, occurs together with harma- 

 line in the seeds of Peganum harmala, and can be sepa- 

 rated from this by subjecting a warm hydrochloric 

 acid solution to partial precipitation with ammonia. 

 It is formed from harmaline by oxidation, when its 

 nitrate is warmed with alcohol and hydrochloric acid ; 

 or from its bichromate, when heated to 120. Colorless 

 shiny prisms, but slightly soluble in water, more easily 

 soluble in alcohol. 



14. Cocaine. 

 C 17 H 21 N0 4 . 



Occurrence. In coca leaves (from Erythroxylon coca). 



Preparation. The leaves are repeatedly extracted 



with water of 60-80 ; the extract precipitated with 



