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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 
 
 

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.[1]

References

  1. Isolation and characterization of products from the nitrosation of the alkaloid gramine. Ahmad, M.U., Libbey, L.M., Barbour, J.F., Scanlan, R.A. Food Chem. Toxicol. (1985) [Pubmed]
 
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