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 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. 1911, 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.