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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, yellow in color, and has little or no taste and odor. It is toxic to the liver and other organs and is a probable human carcinogen. It is also used to create cancer in rats for cancer research.

N-Nitrosodimethylamine
Skeletal formula of N-nitrosodimethylamine
N-Nitrosodimethylamine Ball and Stick.png
N-Nitrosodimethylamine Space Fill.png
Names
Preferred IUPAC name
N,N-Dimethylnitrous amide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.500
EC Number
  • 200-549-8
KEGG
MeSH Dimethylnitrosamine
RTECS number
  • IQ0525000
UN number 3382
Properties
C2H6N2O
Molar mass 74.083 g·mol−1
Appearance Yellow, oily liquid[1]
Odor faint, characteristic[1]
Density 1.005 g/ml
Boiling point 153.1 °C; 307.5 °F; 426.2 K
290 mg/ml (at 20 °C)
log P −0.496
Vapor pressure 700 Pa (at 20 °C)
1.437
Thermochemistry
1.65 MJ/mol
Hazards
Main hazards Known carcinogen[1], extremely toxic
GHS pictograms GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
GHS signal word DANGER
H301, H330, H350, H372, H411
P260, P273, P284, P301+310, P310
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
2
4
0
Flash point 61.0 °C (141.8 °F; 334.1 K)
Lethal dose or concentration (LD, LC):
37.0 mg/kg (oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
OSHA-Regulated Carcinogen[1]
REL (Recommended)
Ca[1]
IDLH (Immediate danger)
Ca [N.D.][1]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

PropertiesEdit

NDMA is a yellow, oily liquid with a faint, characteristic odor and a sweet taste. It is an industrial by-product or waste product of several industrial processes, such as manufacturing of unsymmetrical dimethylhydrazine (UDMH), which is a component of rocket fuel that requires NDMA for its synthesis. Of more general concern, water treatment by chlorination or chloramination of organic nitrogen-containing wastewater can lead to the production of NDMA at potentially harmful levels.[2] Further, NDMA can form or be leached during treatment of water by anion exchange resins.[3] Finally, NDMA is found at low levels in numerous items of human consumption, including cured meat, fish, beer, tobacco smoke[3] and as an impurity in pharmaceuticals.[4] It is, however, unlikely to bioaccumulate.[5]

ToxicityEdit

N-Nitrosodimethylamine is highly toxic, especially to the liver, and is a known carcinogen in lab animals. The EPA classifies NDMA as a probable human carcinogen. The US Environmental Protection Agency has determined that the maximal admissible concentration of NDMA in drinking water is 7 ng/L.[6] The EPA has not yet set a regulatory maximal contaminant level (MCL) for drinking water. At high doses, it is a "potent hepatotoxin that can cause fibrosis of the liver" in rats.[7] The induction of liver tumors in rats after chronic exposure to low doses is well documented.[8] 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 range breaks the N–N bond and can thus be used to degrade NDMA. Additionally, reverse osmosis is able to remove approximately 50% of NDMA.[9]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002) and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.[10]

As a poisonEdit

Several incidents in which NDMA was used to intentionally poison another person have garnered media attention. In 1978, a teacher in Ulm, Germany was sentenced to life in prison for trying to murder his wife by poisoning jam with NDMA and feeding it to her. Both the wife and the teacher later died from liver failure.[11][12]

In 1978, Steven Roy Harper spiked lemonade with NDMA at the Johnson family home in Omaha, Nebraska. The incident resulted in the deaths of 30-year-old Duane Johnson and 11-month-old Chad Shelton. [13] For his crime, Harper was sentenced to death but committed suicide in prison before his execution could be carried out.[14]

In the 2013 Fudan poisoning case, Huang Yang, a postgraduate medical student at Fudan University, was the victim of a poisoning in Shanghai, China. Huang was poisoned by his roommate Lin Senhao, who had placed NDMA into the water cooler in their dormitory. Lin claimed that he only did this as an April Fool's joke. He received a death sentence and was executed in 2015.[15]

Additionally in 2018, NDMA was used in an attempted poisoning at Queen's University in Kingston, Canada.[16]

ReferencesEdit

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0461". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ David L. Sedlak, Rula A. Deeb, Elisabeth L. Hawley, William A. Mitch, Timothy D. Durbin, Sam Mowbray and Steve Carr (2005). "Sources and Fate of Nitrosodimethylamine and Its Precursors in Municipal Wastewater Treatment Plants". Water Environment Research. 77 (1, Emerging Micropollutants in Treatment Systems (Jan.–Feb. 2005)): 32–39. doi:10.2175/106143005X41591. JSTOR 25045835.CS1 maint: uses authors parameter (link)
  3. ^ a b Najm, I.; Trussell, R. R. (2001). "NDMA Formation in Water and Wastewater". Journal American Water Works Association. 93 (2): 92–99. doi:10.1002/j.1551-8833.2001.tb09129.x. ISSN 0003-150X.[permanent dead link]
  4. ^ "Europe recalls generic heart drug made in China on cancer fears". Reuters Health News. Retrieved 13 July 2018.
  5. ^ Liteplo, R.G.; Meek, Bette; Windle, W. (2002). "Concise International Chemical Assessment Document 38: N-nitrosodimethylamine" (PDF). IPCS Concise International Chemical Assessment Documents.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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. CiteSeerX 10.1.1.184.204. doi:10.1089/109287503768335896.
  10. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011. Cite journal requires |journal= (help)
  11. ^ Ein teuflischer Plan: Tod aus dem Marmeladeglas (in German).
  12. ^ Karsten Strey: "Die Welt der Gifte", Lehmanns, 2. Edition p. 193 (in German).
  13. ^ [1]
  14. ^ Roueche, Betron (January 25, 1982). "Annals of Medicine – The Prognosis for this Patient is Horrible". The New Yorker: 57–71.
  15. ^ "15 days log in hospital". Archived from the original on 2014-01-09. Retrieved 2013-04-30.
  16. ^ Man admits to poisoning fellow researcher in Kingston.

External linksEdit