6637. N-Nitrosodimethylamine

Nomenclature

CAS number: 62-75-9
N-Methyl-N-nitrosomethanamine; dimethylnitrosamine; DMN; DMNA.
C2H6N2O; mol wt 74.08.
C 32.43%, H 8.16%, N 37.82%, O 21.60%.

Description and references

Reportedly found in trace amounts in tobacco smoke condensates: Rhoades, Johnson, Nature 236, 307 (1972); in cured meat products, notably bacon: Sen et al., ibid. 241, 473 (1973); in smoked and salted fish: Fazio et al., J. Agric. Food Chem. 19, 250 (1971); Fong, Chan, Nature 243, 421 (1973). Formed by the interaction of nitrite with dimethylamine and by the action of nitrate-reducing bacteria. Industrial prepn: GB 772331 (1957 to Olin Mathieson), C.A. 51, 14783a (1957); Ioffe, Zh. Obshch. Khim. 28, 1296 (1958); Norris, J. Am. Chem. Soc. 81, 3346 (1959); Campbell, US 2981752 (1961 to C.S.C.); Datin, Elliott, US 3136821 (1964 to Allied Chem.). Chemistry: Layne et al., J. Am. Chem. Soc. 85, 435, 1816 (1963). Metabolism and toxicity: Magee, Vandekar; Magee, Biochem. J. 70, 600, 606 (1958); Heath, ibid. 85, 72 (1962). Carcinogenicity studies: Magee, Barnes, Br. J. Cancer 10, 114 (1956); see also eidem, Adv. Cancer Res. 10, 163-246 (1967). Review of toxicology and human exposure: Toxicological Profile for N-Nitrosodimethylamine (PB90-182130, 1989) 132 pp.

Chemical structure

Properties

Yellow liquid. bp 151-153°. bp40 67.1°. d420 1.0048. nD20 1.4368. Very sol in water, alcohol, ether. LD50 i.p. in rats: 34 mg/kg (Heath).

Caution

Potential symptoms of overexposure are nausea, vomiting, diarrhea and abdominal cramps; headache; fever; enlarged liver, jaundice; reduced function of liver, kidneys and lungs. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 232. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-199.

Use

Formerly in the prodn of rocket fuels; antioxidant; additive for lubricants; softener of copolymers.