title: Nitrosation of N-methyltyramine and N-methyl-3-aminomethylindole, two barley malt alkaloids.
abstract: The secondary amine barley malt alkaloids N-methyltyramine and N-methyl-3-aminomethylindole were synthesized, nitrosated in dilute acetic acid and the products characterized by mass spectrometry and NMR spectroscopy. The nitrosation products of N-methyltyramine were p-hydroxy-m-nitro-N-nitroso-N-methyl-2-phenylethylamine and p-hydroxy-N-nitroso-N-methyl-2-phenylethylamine. Upon nitrosation, N-methyl-3-aminomethylindole formed N-nitroso-N-methyl-3-aminomethylindole and the dinitrosated product N1-nitroso-N-nitroso-N-methyl-3-aminomethylindole.
mesh_terms: D000470:Alkaloids; D002523:Edible Grain / Q000032:analysis*; D001467:Hordeum / Q000032:analysis*; D007211:Indoles / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009602:Nitrosamines / Q000138:chemical synthesis; D014439:Tyramine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000470:Alkaloids; D007211:Indoles; D009602:Nitrosamines; C036245:N-methyl-3-aminomethylindole; C036243:N-nitroso-N-methyltyramine; C036246:N-nitroso-N-methyl-3-aminomethylindole; C036247:N'-nitroso-N-nitroso-N-methyl-3-aminomethylindole; C036244:methyl-4-tyramine; D014439:Tyramine