N-Nitrosamides
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| Basic structure with blue emphasized functional group |
N-Nitrosamide derivates with blue emphasized functional group |
 N-Nitrosamides |
 N-Nitrosocarbamates
|
| R1-R3 are hydrogen atoms or organic residues | |
Nitrosamides are chemical compounds that contain the chemical structure R1C(=X)N(–R2)–N=O, that is, a nitroso group bonded to the nitrogen of an amide or similar functional group.[1] Specific classes include the N-nitrosamides, N-nitrosoureas, N-nitrosoguanidines, and N-nitrosocarbamates. Nitrosamides are usually chemically reactive, metabolically unstable,[1] and often carcinogenic; however, in contrast to the N-nitrosamines, N-nitrosamides are not generally contaminants found in food.[1]
Various chloroethylnitrosoureas (such as N, N'-bis (2-chloroethyl)nitrosourea, BCNU) have obtained a medical use in the field of malignant tumors.[2] It is hypothesized that the efficacy against cancer cells is based on the alkylability of guanine cytosine centers in the sequences of the genetic material, especially the oncogenes.[2]
Synthesis
N-Nitrosamides can be prepared starting from N-monosubstituted carboxamides and the nitrosyl cation (which results from the nitrous cation in the presence of strong acids from the nitrous acid), here exemplified for N-methylacetamide (1).[3][4] The carboxamide reacts in a nucleophilic attack at the nitrosyl cation. After the elimination of a proton, an N-nitrosamide (2) is formed from the resulting cation:
