N-Nitrosodimethylamine

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Not to be confused with MDMA or NMDA.
NDMA redirects here. For the Pakistani government disaster management organisation, see National Disaster Management Authority.
N-Nitrosodimethylamine
Skeletal formula of N-nitrosodimethylamine
Identifiers
CAS number 62-75-9 YesY
PubChem 6124
ChemSpider 5894 N
EC number 200-549-8
UN number 3382
KEGG C14704 N
MeSH Dimethylnitrosamine
ChEBI CHEBI:35807 N
ChEMBL CHEMBL117311 N
RTECS number IQ0525000
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C2H6N2O
Molar mass 74.08 g mol−1
Appearance Yellow, transparent liquid
Density 1.005 g mL−1
Boiling point 153.1 °C; 307.5 °F; 426.2 K
Solubility in water 290 mg mL−1 (at 20 °C)
log P −0.496
Vapor pressure 700 Pa (at 20 °C)
Refractive index (nD) 1.437
Thermochemistry
Std enthalpy of
combustion
ΔcHo298
1.65 MJ mol−1
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H301, H330, H350, H372, H411
GHS precautionary statements P260, P273, P284, P301+310, P310
EU Index 612-077-00-3
EU classification Very Toxic T+ Dangerous for the Environment (Nature) N
R-phrases R45, R25, R26, R48/25, R51/53
S-phrases S45
Flash point 61.0 °C (141.8 °F; 334.1 K)
LD50 37.0 mg kg−1 (oral, rat)
Related compounds
Related amines
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is a semi-volatile organic chemical, produced as by-product of several industrial processes and present at very low levels in certain foodstuffs, especially those cooked, smoked, or cured. NDMA is water-soluble, colorless, and its taste and odor are weak or absent. It is toxic to the liver and other organs.

Properties[edit]

NDMA is an industrial by-product or waste product of several industrial processes. Manufacturing of unsymmetrical dimethylhydrazine (UDMH), which is a component of rocket fuel that requires NDMA for its synthesis, proved to be the culprit in these cases. Of more general concern, water treatment via chlorination or chloramination of organic nitrogen-containing wastewater can lead to the production of NDMA at potentially harmful levels.[1] Further, NDMA can form or be leached during treatment of water by anion exchange resins.[2] Finally, NDMA is found at low levels in numerous items of human consumption including cured meat, fish, beer, and tobacco smoke[2] It is, however, unlikely to bioaccumulate.

Toxicity[edit]

N-Nitrosodimethylamine is highly toxic, especially to the liver, and is a suspected human carcinogen. The US Environmental Protection Agency has determined that the maximum admissible concentration of NDMA in drinking water is 7 ng L−1.[3] The EPA has not yet set a regulatory maximum contaminant level (MCL) for drinking water. At high doses, it is a "potent hepatotoxin that can cause fibrosis of the liver" in rats.[4] The induction of liver tumors in rats after chronic exposure to low doses is well documented.[5] Its toxic effects on humans are inferred from animal experiments but not well-established experimentally.

NDMA's contamination of drinking water is of particular concern due to the minute concentrations at which it is harmful, the difficulty in detecting it at these concentrations, and to the difficulty in removing it from drinking water. It does not readily biodegrade, adsorb, or volatilize. As such, it cannot be removed by activated carbon and travels easily through soils. Relatively high levels of UV radiation in the 200 to 260 nm breaks the N-N bond and can thus be used to degrade NDMA. Additionally, reverse osmosis is able to remove approximately 50% of NDMA.[6]

As a Poison[edit]

On September 10, 1978, Steven Roy Harper, a jealous former boyfriend of Sandra Johnson, spiked lemonade with NDMA at the Johnson family home in Omaha, Nebraska. Harper had acquired NDMA working at the UNMC Eppley Cancer Center in March 1978. At the time, this substance was in common use in the laboratory to induce cancer in mice for study. The incident resulted in the death of 11-month-old Chad Sheldon and 30-year old Duane Johnson from, ultimately, massive liver damage. NDMA produced very characteristic lesions in the liver, rapidly declining platelet count, and highly elevated SGOT levels. Other symptoms included headache, fever, vomiting, abdominal pain, scattered intradermal hemorrhage, lethargy, nausea, and diarrhea.[7]

Huang Yang (Chinese: 黄洋; pinyin: Huáng Yáng, 1985 – April 16, 2013), age 28, a postgraduate medical student at Fudan University was the victim of a N-Nitrosodimethylamine poisoning in Shanghai, China. Huang is believed to have been poisoned by his roommate via a dispenser in his dormitory on April 1, 2013. Huang was critically ill within hours. A few days later, investigators established Huang had ingested NDMA. He died in 15 days after getting sick. His roommate, another medical student who had written several papers on NDMA, was detained and is the only suspect.[8][9] In the progression of the poisoning, his liver function had been damaged in Day 2, blood platelet levels fell in Day 3, nose first started bleeding in Day 5, and he fell into a coma in Day 8. His pupils dilated in Day 14, and he suffered from pulmonary fibrosis in Day 15.[10]

References[edit]

  1. ^ ""Sources and Fate of Nitrosodimethylamine and Its Precursors in Municipal Wastewater Treatment Plants". David L. Sedlak, Rula A. Deeb, Elisabeth L. Hawley, William A. Mitch, Timothy D. Durbin, Sam Mowbray and Steve Carr. Water Environment Research Vol. 77, No. 1, Emerging Micropollutants in Treatment Systems (Jan. - Feb., 2005), pp. 32-39. Published by: Water Environment Federation". Retrieved March 13, 2013. 
  2. ^ a b Najm, I.; Trussell, R. R. (2001). "NDMA Formation in Water and Wastewater". Journal American Water Works Association 93 (2): 92–99. ISSN 0003-150X. 
  3. ^ Andrzejewski, P.; Kasprzyk-Hordern, B.; Nawrocki, J. (2005). "The hazard of N-nitrosodimethylamine (NDMA) formation during water disinfection with strong oxidants". Desalination 176 (1–3): 37–45. doi:10.1016/j.desal.2004.11.009. 
  4. ^ George, J.; Rao, K. R.; Stern, R.; Chandrakasan, G. (2001). "Dimethylnitrosamine-induced liver injury in rats: the early deposition of collagen". Toxicology 156 (2–3): 129–138. doi:10.1016/S0300-483X(00)00352-8. PMID 11164615. 
  5. ^ Peto, R.; Gray, R.; Brantom, P.; Grasso, P. (1991). "Dose and Time Relationships for Tumor Induction in the Liver and Esophagus of 4080 Inbred Rats by Chronic Ingestion of N-Nitrosodiethylamine or N-Nitrosodimethylamine" (pdf). Cancer Research 51 (23 Part 2): 6452–6469. PMID 1933907. 
  6. ^ Mitch, W. A.; Sharp, J. O.; Trussell, R. R.; Valentine, R. L.; Alvarez-Cohen, L.; Sedlak, D. L. (2003). "N-Nitrosodimethylamine (NDMA) as a Drinking Water Contaminant: A Review". Environmental Engineering Science 20 (5): 389–404. doi:10.1089/109287503768335896. 
  7. ^ Roueche, Betron (January 25, 1982). "Annals of Medicine - The Prognosis for this Patient is Horrible". The New Yorker: 57–71. 
  8. ^ Roommate held after Shanghai student dies from poisoning
  9. ^ Poisoning, death of Fudan student recalls disturbing case of Zhu Ling
  10. ^ 15 days log in hospital

External links[edit]