6636. N-Nitrosodiethylamine

Nomenclature

CAS number: 55-18-5
N-Ethyl-N-nitrosoethanamine; diethylnitrosamine; DEN; DENA; NDEA.
C4H10N2O; mol wt 102.14.
C 47.04%, H 9.87%, N 27.43%, O 15.66%.

Description and references

Detected in trace amounts in tobacco smoke: Druckney, Preussman, Naturwissenschaften 49, 498 (1962) DOI; and in various processed foods: Hedler, Marquardt, Food Cosmet. Toxicol. 6, 341 (1968) DOI PubMed; Friemuth, Glaeser, Nahrung 14, 357 (1970) DOI. Formed by the interaction of nitrite with diethylamine and by the action of nitrate-reducing bacteria. Industrial prepn: Reilly, DE 1085166 (1960 to du Pont), C.A. 56, 4594h (1962); Levering, Maury, US 3090786 (1963 to Hercules Powder); Minisci, Galli, Chim. Ind. (Milan) 46, 173 (1964). Hepatotoxicity and carcinogenicity studies: Schmaehl et al., Naturwissenschaften 54, 341 (1967); Grover, Fischer, Eur. J. Cancer 7, 77 (1971) PubMed; Bader et al., Arch. Geschwulstforsch. 37, 327 (1971) PubMed. General review: Magee, Barnes, Adv. Cancer Res. 10, 163-246 (1967) DOI PubMed.

Chemical structure

Properties

Slightly yellow liq. d420 0.9422. bp 175-177°. bp5 47°. nD20 1.4388. Sol in water, alc, ether.

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-198.

Use

Gasoline and lubricant additive; antioxidant; stabilizer in plastics.