INDIAN MEDICINAL PLANTS. 
240 
cautiously to 60,° and then setting it aside; it tnclts at 204-205.° Methyl- 
harmaline, prepared from hartnaline methiodide by boiling it with baryta 
water, melts and decomposes at 162°, and will unite with more methylic 
iodide. Dihydroharuialinc is best prepared by reducing hartnaline with 
sodium in boiling amyl-alcohoiio solution ; its acetyl .and benzoyl derivatives, 
C, 3 H 15 AeN 2 0, etc., melt at 239’ and 158-159° respectively. Harminc and 
harmalinc are oxidised to liarminic acid, C 10 H a N 2 O 4 , by chromic acid in 
boiling acetic acid solution, or by nitric acid, the same product being obtained 
when harmol, dichloroharmiiie, 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 nujthl Uuvmillic acid, C, 0 H 7 McN 2 0 4 , which can also be obtained 
by the oxidation of methyl'iarmibe, and which blackens between 260° and 280° 
when heated ; with ethylic iodide, it yields cthijlharminic acid, ^ 10 ^ 7 ^ N,0 4 , 
which blackens at 280°. Apoharuiine, formed from liarminic acid by the loss 
of 2 mols. of carbonic anhydride, yields a yellow pi [crate melting at 247,° 
boiling concentrated nitric acid converts it into a derivative, C„H 7 (NO,) N,, 
which melts and decomposes at 270 , aud is soluble in alkalis ; with methylic 
iodide, it yields the hydriodide of mcthijlapohar mine, C„H 7 MeN 2 , which base 
melts at 77-7t°, and yields a yellow plutiitochloride which decomposes at 260°. 
J. Ch.. S. 1898 A. I. 164. 
Harmalol has been isolated from the seeds of Pegunum harmala, and is 
identical with the product obtained by the action of concentrated hydro- 
chloric acid on harinaliue ; the green fluorescence of its aqeuous solution 
is almost completely destroyed by acids or alkalis. Harmine melts at 
257-259°. liarminic 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 permanganato, forming ammonia and 
oxalic acid ; its nitro-derivative has both acid and basic properties (compare 
the uitroiminazoles of Bamberger and Berle). The auroehloridc crystallises 
in orange yellow needles concentrically arranged. Harmol can not be directly 
reduced by the action of hydriodiq acid or of zine dust, but the oxygen may 
bo eliminated indirectly by means of the amino-deravative. 
Aminoharman, C 12 H U 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 at 298°, 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 3 , obtained by diazotising the amino-derivative, '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 inochlorUle, (C 12 H 10 N 3 ) 2 , H 2 PtCl 6 , $H 2 0, 
