2W) INDIAN MEDICINAL PLANTS. 



cautiously to 60, c and then setting it aside ; it melts at 204-205.° Methyl- 

 karmaline, prepared from harmaline methiodide by boiling it with baryta 

 water, melts and decomposes at 162°, and will unite with more methylic 

 iodide. Dihydroharuialine is best prepared by reducing harmaline with 

 sodium in boiling amyl-alcoholic solution ; its acetyl and benzoyl derivatives, 

 C 13 H 15 AeX 2 0, etc., melt at 239' and 158-159° respectively. Harmine and 

 harmaline are oxidised to harminic acid, C 10 H 3 N 2 O 4 , 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 mythl harminic acid, C l0 H 7 MeN 2 O 4 , which can also be obtained 

 by the oxidation of methyl'iarmine, and which blackens between 260° and 280° 

 when heated ; with ethylic iodide, it yields ethylharminic acid, C 10 H 7 Et N 2 4 , 

 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, C d H 7 (N0 2 ) N 2 , 

 which melts and decomposes at 270°, and is soluble in alkalis ; with methylic 

 iodide, it yields the hydriodide of methylapoharmine, C b H 7 MeN 2 , which base 

 melts at 77-7i>°, and yields a yellow platinochloride which decomposes at 260°, 

 J. Ch. S. 189S A. I, 161. 



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 , |H 2 0, 



