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246 cautiously to 60°, c and then setting it aside ; it melts at 204-205°. Methyl-harmaline, prepared from harmaline methiodide by boiling it with baryta water, melts and decomposes at 162°, and will unite with more methylic iodide. Dihydroharmaline is best prepared by reducing harmaline with sodium in boiling amyl-alcoholic solution ; its acetyl and benzoyl derivatives, C13H15 AcN2O, etc., melt at 239° and 158-159° respectively. Harmine and harmaline are oxidised to harminic acid, C10H8N2O4, by chromic acid in boiling acetic acid solution, or by nitric acid, the same product being obtained when harmol, dichloroharmine, or introharmine is oxidised. This acid reacts with normal alkali like a monobasic acid, but with resorcinol, like a dibasic acid, forming a fluorescein. It reacts with methylic iodide and aqueous potash, yielding mythlharminic acid, C10H7MeN2O4, which can also be obtained by the oxidation of methylharmine, and which blackens between 260° and 280° when heated ; with ethylic iodide, it yields ethylharminic acid, C1H7Et N2O4, which blackens at 280°. Apoharmine, formed from harminic acid by the loss of 2 mols. of carbonic anhydride, yields a yellow picrate melting at 247,° boiling concentrated nitric acid converts it into a derivative, C8 H7(NO2)N2, which melts and decomposes at 270°, and is soluble in alkalis ; with methylic iodide, it yields the hydriodide of methylapoharmine, C8H7MeN2, which base melts at 77-78°, and yields a yellow platinochloride which decomposes at 260°, J. Ch. S. 189S A. I, 164.

Harmalol has been isolated from the seeds of Peganum harmala, and is identical with the product obtained by the action of concentrated hydro- chloric acid on harmaline ; the green fluorescence of its aqeuous solution is almost completely destroyed by acids or alkalis. Harmine melts at 257-259". Harminic acid is an ortho-dicarboxylic acid, but on titration behaves like a monobasic acid, one carboxyl group being combined as in a salt. Apoharmine is decomposed by potassium permanganate, forming ammonia and oxalic acid ; its nitro-derivative has both acid and basic properties (compare the nitroiminazoles of Bamberger and Berle). The aurochloride crystallises in orange yellow needles concentrically arranged. Harmol can not be directly reduced by the action of hydriodic acid or of zinc dust, but the oxygen may bo eliminated indirectly by means of the amino-deravative.

Aminoharman, C 12 H n N 3, prepared by the action of ammonio-zinc chloride and ammonium chloride on harmol at 250°, crystallises from water in flat needles or leaflets, has a silvery lustre, sinters at 292°, melts at298 ci, sublimes with partial decomposition, and is easily soluble in alcohol. The solutions of the salts show a blue fluorescence. The hydrochloride crystallises in colourless prisms, and is slightly soluble in water ; the nitrate aud sulphate were also prepared.

Harman, C 12 H 10 N 2, obtained by diazotising the amino-dcrivative, re- sembles harmine, and separates in leaflets or flat needles ; it crystallises from benzene in small stout crystals, melts at 230°, sublimes with partial decomposition, forming a sublimate which crystallises in needles, and is readily soluble in ethyl or methyl alcohol. Its solution in concentrated sulphuric acid has a faint blue fluorescence, whilst the solutions of its salts show a strong blue fluorescence. The plat inochloride, (C 12 H I0 N 2 ) 2, H 2 PtCl d ,