Isolation and characterization of products from the nitrosation of the alkaloid gramine.
The nitrosation of gramine, a tertiary amine alkaloid present in barley malt, was carried out by reaction with sodium nitrite in buffered acetic acid (pH 3.4) for 1 hr at room temperature. Two major non-volatile products of the nitrosation reaction were isolated by preparative HPLC and characterized as indole-3-carboxylic acid and N1-nitroso-3-nitromethylindole. This interpretation was supported by spectral data. The nature of these products indicated that gramine did not undergo nitrosation by the expected mechanism of nitrosative dealkylation. A mechanism is offered to explain the labile nature of the dimethylamino group found in gramine.
D000470:Alkaloids; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D026121:Indole Alkaloids; D007211:Indoles / Q000032:analysis; D007536:Isomerism; D009573:Nitrites; D012977:Sodium Nitrite
D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D009573:Nitrites; C012382:indole-3-carboxylic acid; C046813:N(1)-nitroso-3-nitromethylindole; C007884:gramine; D012977:Sodium Nitrite