N-Nitrosodimethylamine
- NDMA redirects here. For the Pakistani government disaster management organisation, see National Disaster Management Authority.
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| N-Nitrosodimethylamine | |
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| Identifiers | |
| CAS number | 62-75-9  |
| PubChem | 6124 |
| ChemSpider | 5894  |
| EC number | 200-549-8 |
| KEGG | C14704 |
| MeSH | Dimethylnitrosamine |
| ChEBI | CHEBI:35807 |
| ChEMBL | CHEMBL117311 |
| RTECS number | IQ0525000 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C2H6N2O |
| Molar mass | 74.08 g mol−1 |
| Appearance | Yellow, transparent liquid |
| Density | 1.005 g mL−1 |
| Boiling point |
153 °C, 426.2 K, 307 °F |
| 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 ΔcH |
1.65 MJ mol−1 |
| Hazards | |
| GHS pictograms |    |
| 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 |  T+  N |
| R-phrases | R45, R25, R26, R48/25, R51/53 |
| S-phrases | S45 |
| Flash point | 61.0 °C |
| LD50 | 37.0 mg kg−1 (oral, rat) |
| Related compounds | |
| Related amines | |
| Related compounds | |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is a semi-volatile organic chemical that is highly toxic 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.[1] 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.[2] The induction of liver tumors in rats after chronic exposure to low doses is well documented.[3] Its toxic effects on humans are inferred from animal experiments but not well-established experimentally.
NDMA appears to have a very strong affinity as a poison for the liver and at least one case of poisoning in humans is reported. NDMA is water-soluble, colorless, and has at best a weak taste and odor. In the incident reported by New Yorker writer Berton Roueché, a jealous former boyfriend spiked lemonade with NDMA, which he had acquired while working at a cancer research center. At the time of writing, this substance was in common use in the laboratory to induce cancer in mice for study. The incident resulted in the death of an 11-month-old male child and a 30-year old man from, ultimately, massive liver damage. In the victims, 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.[4]
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.[5] Further, NDMA can form or be leached during treatment of water by anion exchange resins.[6] Finally, NDMA is found at low levels in numerous items of human consumption including cured meat, fish, beer, and tobacco smoke[6] It is, however, unlikely to bioaccumulate.
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.[7]
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Famous uses as a poison [edit]
Chinese medical school student poisoning [edit]
Huang Yang (Chinese: 黄洋; pinyin: Huáng Yáng, 1985 – April 16, 2013) 28, a postgraduate medical student at Fudan University was the victim of N-Nitrosodimethylamine poisoning in Shanghai, China. Yang is believed in getting poisoned by his roommate by having drank water from a dispenser in his dormitory on April 1, 2013 and he was critically ill within hours. A few days later, investigators established Huang had ingested N-Nitrosodimethylamine (NDMA), a toxic compound that is the by-product of a number of chemical processes. He died in 15 days after getting sick. His room-mate, another medical student who had written several papers on NDMA, was detained and is the only suspect.[8][9]
With in 15 days, his liver function had been damaged in Day 2. Rate of blood platelet levels fell in Day 3. Nose first started bleeding in Day 5. He fell into a coma in Day 8. 11 April 2013, Huang was announced to be in critical condition. His pupils dilated in Day 14. He was suffering from pulmonary fibrosis in Day 15.[10]
References [edit]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Roueche, Betron (January 25, 1982). "Annals of Medicine - The Prognosis for this Patient is Horrible". The New Yorker: 57–71.
- ^ ""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.
- ^ 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.
- ^ 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.
- ^ Roommate held after Shanghai student dies from poisoning
- ^ Poisoning, death of Fudan student recalls disturbing case of Zhu Ling
- ^ 15 days log in hospital
