n. o. RtmrR.E. 
247 
crystallises in pale yellow needles jnd is slightly soluble in water, the 
auricliloride separating in matted, orange needles and the mcrcurichloridc was 
also prepared. 
Harmaline crystnllises 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. Ry the action of 
hydrochloric acid on a boiling solution of acetyl-harmaline in alcohol, the 
solution becomes brown, green and finally dirty blue, and from the product 
ammonia precipitates a strong bnse, C H If 13 0 3 N 2 , in almost colourless needles 
or leaflets; it separates from water in yellow crystals, melts at 104 — 105'. 
is easily soluble in hot water, and forms yellow solutions in acids. The 
platinichloride, (0 15 H 13 0 3 N 5 ) 2 ,H 1 PtCI 5 , crystallises in lustrous, brown needles, 
and decomposes at 210°. The auricliloride is difficult to obtain in a crystalline 
form. The mercurichloride was also prepared. The base is only reconverted 
into harmaline by prolonged boiling with alcoholic potash, and by the action 
of hydrochloric acid at 150 —160° it forms harmalol. When harmaline is boiled 
with nitric acid of sp. gr. 1'48, nitroanisic acid [OMe : NOj : CO,H=l : 2 : 4] 
is formed together with harminic acid. The former acid is derived from 
methoxy- nitrophthalic acid by elimination of carbon dioxide. The harmaline 
alkaloids must therefore contain a complex, OMe.C„Hj(C — C, in which OMe: 
C:C=l : 3:4 or l : 4: 5. 
The physiological effect of these alkaloids is to reduce the temperature. 
J. Ch. S. 1001 A. 1. pp. 405-406. 
The physiological action of some of the derivatives was investigat- 
ed, namely, harmiue (C^H^ON,), harmaline (C ls H u ON 7 ), dihydroharmaline 
(C l3 H„ON 2 ),andapoharmine (CjHyN,). The first three have a paralysing action 
on frogs, whilst opoharmine causes increased reflex irritability and tetanus. 
Harmine and harmaline paralyse the skeletal and cardiac muscle of the frog. 
Harmaline has an anthelmintic action, probably by paralysing the musculature 
of the parasites. In warm-blooded animals, harmino and harmaliue 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 system), and partly 
excreted by the kidneysand intestine. 
J. Ch. S. 1911. A. It. p. 138. 
On treating harmatine, harmine, apoharmine, and mothylapoharmine with 
bromine in acetic acid, the hydrobromides of the corresponding monobromo- 
derivatives are obtained. Bromoharmaline, Ci S R 13 ON 2 Br, crystallises in 
colourless, slender needles, m. p. 195° ; the hydrochloride and platinichloride 
are yellow. In the case of harmino, two isomeric compounds are formed, and 
may be separated by heating the hydrobromides at 50°, bromoharmine hydrobro- 
mide alone fusing at this tomperature. Bromoharmine, C 13 H u ON.jnr, occurs 
in orthorhombic prisms, m. p. 275°; the salts crystallise from alcohol, but 
form jellies with water. isoBromoharmine crystallises in long needles, m. p. 
208°, and its salts crystallise from water ; the platinichloride is orange-red. 
