N-nitrosodibenzylamine

Chemical properties

Yellow Low Melting Solid

The Uses of N-nitrosodibenzylamine

N-Nitrosodibenzylamine (NDBzA) is mutagenic to Salmonella typhimurium and induces DNA strand breaks in isolated rat hepatocytes.

What are the applications of Application

N-Nitrosodibenzylamine is a mutagenic to Salmonella typhimurium

Production Methods

Human exposure to NDBzA was not suspected, but then there were reports of the compound in hams wrapped in rubber netting. Concentrations of NDBzA from 10 to 100 ppb were common, and some were as high as 512 ppb. Like other nitrosamines in rubber, NDBzA arose by nitrosation of dialkylamino compounds (in this case dibenzyl-) during manufacture.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 2619, 1984 DOI: 10.1016/S0040-4039(01)81245-4

Safety Profile

Moderately toxic by ingestion.Mutation data reported. When heated to decomposition itemits toxic vapors of NOx

Carcinogenicity

There is a single report of a test of nitrosodibenzylamine for carcinogenicity in rats using high doses and that is completely negative; in contrast, nitrosobenzylphenylamine is a weak, but definite, esophageal carcinogen in rats. NDBzA is not mutagenic to bacteria in the presence or absence of rat liver microsomes.
Although there is no information about metabolism and activation of NDBzA, the alpha-acetoxy derivative (which presumably is the ester of the alpha-hydroxy derivative that would be formed in vivo) is both carcinogenic to rats and mutagenic to bacteria.