Harmine salts

Harmine, C13H12ON2, crystallises from methyl alcohol in colourless rhombic prisms, m.p, 266°, [a]D 0°. The hydrochloride, m.p. 269-5-270-5° (Chen ), nitrate, platinichloride, m.p. 264-6°, acid chromate and oxalate crystallise well. The salts show a deep blue fluorescence in dilute solution. Harmine behaves as a monoacidic base. It gives a methiodide, from which methylharmine, needles, m.p. 209°, may be prepared, and this in turn yields methylharmine methiodide. On demethylation harmine yields the phenolic base harmol, C12H10ON2, m.p. 321°.i ... 

The alkylation of carboline derivatives has been repeatedly studied. The first quaternary A-alkyl carbolinium salts to be described were those prepared in connection with the elucidation of the structure of harmine (methiodide, methochloride, and methosulfate Other j8-carbolinium salts were subsequently prepared in connection with systematic studies of the site of alkylation and of the... 

The intense fluorescence of /3-carbolmium salts has been repeatedly noted (see, e.g., ref. 3). The wavelengths for maximum activation and emission of fluoreseenee have been determined for harmine, ... 

Michael Valentine Smith suggests in Psychedelic Chemistry that harmaline and harmine are both active at about 200 mg. oral dosage. Jeremy Bigwood disputes this, saying that to get effective potentiation from the hydrochloride salts an adult should swallow at least 300 mg, harmaline or 500 mg. harmine. Shulgin puts the "effective dose range of harmaline at 70 to 100 mg. intravenously or 300 to 400 mg. orally. 

Harmaline and harmine are both crystalline, the first appearing as yellow and the second as green hydrochloride salts. According toHoffer and Osmond, both form these salts... 

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