N. 0. RUTAOEiE. 247 



crystallises in pale yellow needles and is slightly soluble in water, the 

 aiirichloride separating in matted, orange needles and the mere urichloride was 

 also prepared. 



Harmaline crystallises from alcohol or benzene in large, colourless 

 crystals which, in thicker layers, appear yellow. Its solution in concentrated 

 sulphuric acid is intensely yellow but not fluorescent, whilst the alcoholic 

 solutions of the yellow salts have a green fluorescence. By the action of 

 hydrochloric acid on a boiling solution of acetyl-harmaline in alcohol, the 

 solution becomes brown, greeu and finally dirty blue, and from the product 

 ammonia precipitates a strong base, C 15 H l8 3 N 2 , in almost colourless needles 

 or leaflets; it separates from water in yellow crystals, melts at 164—165°, 

 is easily soluble in hot water, and forms yellow solutions in acids. The 

 platinichloride, (C lS H l3 3 N 2 ) 2 ,H 2 PtCl 6 , crystallises in lustrous, brown needles, 

 and decomposes at 210°. The aiirichloride is difficult to obtain in a crystalline 

 form. The mercurichloride was also prepared. The base is only reconverted 

 into harrnaline by prolonged boiling with alcoholic potash, and by the action 

 of hydrochloric acid at 150 — 160° it forms harmalol. When harrnaline is boiled 

 with nitric acid of sp. gr. 1'48, nitroanisic acid [OMe : N0 2 : C0 2 H— 1 : 2 : 4] 

 is formed together with harminic acid. The former acid is derived from 

 methoxy- nitrophthalic acid by elimination of carbon dioxide. The harrnaline 

 alkaloids must therefore contain a complex, OMe.C -H 3 (C — )C, in which OMe: 

 C : C^rl : 3 : 4 or 1 : 4 : 5. 



The physiological effect of these alkaloids is to reduce the temperature. 



J. Ch. S. 1901 A. I. pp. 405-406. 

 The physiological action of some of the derivatives was investigat- 

 ed, namely, harmine (C 13 H 12 ON 2 ), harrnaline (C 13 H 14: ON 2 ), dihydroharmaline 

 (C 13 H 16 ON 2 ), and apoharmine (C a H 8 N 2 ). The first three have a paralysing action 

 on frogs, whilst Apoharmine causes increased reflex irritability and tetanus. 

 Harmine and harrnaline paralyse the skeletal and cardiac muscle of the frog. 

 Harrnaline has an anthelmintic action, probably by paralysing the musculature 

 of the parasites. In warm-blooded animals, harmine and harmaline cause 

 convulsions, increase of saliva, interference with respiration, and depression 

 of temperature. In the East the seeds are used as a substitute for hashish, 

 and in dogs it is evident that psychic disturbances occur. The drugs are 

 partly destroyed in the body (blood, liver, and nervous sj^stem), and partly 

 excreted by the kidneys and intestine. 



J. Ch. S. 19ll, A. II. p. 138. 



On treating harmaline, harmine, apoharmine, and methylapoharinine with 

 bromine in acetic acid, the hydrobromides of the corresponding monobromo- 

 derivatives are obtained. Bromoharmaline, Ci 3 H ]3 ON 2 Br, crystallises in 

 colourless, slender needles, m. p. 195° ; the hydrochloride, and platinichloride 

 are yellow. In the case of harmine, two isomeric compounds are formed, and 

 may be separated by heating the hydrobromides at 50°, bromoharmine hydrobro- 

 mide alone fusing at this temperature. Bromoharmine, C l3 H n ON 2 Br, occurs 

 in orthorhombic prisms, m. p. 275°; the salts crystallise from alcohol, but 

 form jellies with water. /soBromoharmine crystallises in long needles, m. p. 

 203°, and its salts crystallise from water ; the jilatimchloridc is orange-red. 



