Nor-harmane

In view of its possible interest as the mode of formation of harman, harmine and harmaline in plants, Kermack, Perkin and Robinson investigated the conversion of tryptophan (II) into harman (I) and nor-harman (IV). The latter is produced when tryptophan is condensed with formaldehyde in presence of dilute sulphuric acid and the product (III) oxidised by potassium dichromate. Harman is formed when formaldehyde in this process is replaced by acetaldehyde. 

Y. Fukuyama, A. D. Kolender, M. Nishioka, H. Nonami, M. C. Matulewicz, R. Erra-Balsells, and A. S. Cerezo, Matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry of / -(l—>3), f-( 1 —>4)-xylans from Nothogenia fastigiata using nor-harmane as matrix, Rapid Com-mun. Mass Spectrom., 19 (2005) 349-358. 

R. Erra-Balsells and H. Nonami, UV-MALDI-TOF MS analysis of carbohydrates. Reviewing comparative studies performed using nor-harmane and classical UV-MALDI matrices, Environ. Control Biol., 46 (2008) 65-90. 

Photochemical behaviour of full-aromatic jS-carbo-lines, nor-harmane, harmane and harmine in chloroform medium and the corresponding UV absorption and fluorescence emission spectra have been discussed. Irreversible electron transfer from the singlet excited /3-carboline molecule to the chloroform molecule in the transient excited charge transfer complex has been proposed as the primary photochemical process initiating the mechanism of secondary reactions in this system. 

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