Nitrosamine: Difference between revisions
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Revision as of 15:57, 30 September 2009
Nitrosamines are chemical compounds of the chemical structure R1N(-R2)-N=O, some of which are carcinogenic.
Usages
- Most rubber products
- Pesticides
- Certain cosmetics
Occurrences
Food
Nitrosamines are produced from nitrites and secondary amines, which often occur in the form of proteins. Their formation can occur only under certain conditions, including strongly acidic conditions such as that of the human stomach. High temperatures, as in frying, can also enhance the formation of nitrosamines. These cooking styles may be responsible for thousands of cases of colon cancer per year across the world. The presence of nitrosamines may be identified by the Liebermann's reaction. [1]
Under acidic conditions the nitrite forms nitrous acid (HNO2), which is protonated and splits into the nitrosonium cation N≡O+ and water: H2NO2+ = H2O + NO+. The nitrosonium cation then reacts with an amine to produce nitrosamine.[citation needed]
Nitrosamines are found in many foodstuffs, especially beer, fish, and fish byproducts, and also in meat and cheese products preserved with nitrite pickling salt. The U.S. government established limits on the amount of nitrites used in meat products in order to decrease cancer risk in the population. There are also rules about adding ascorbic acid or related compounds to meat, because they inhibit nitrosamine formation.[citation needed]
Consumer products
Nitrosamines can be found in tobacco smoke, American dip snuff and to a much lesser degree, snus. (127.9 PPM for American dip snuff compared to 2.8 PPM in Swedish snuff or snus.)[2]
It is also found in latex products. A test of party balloons and condoms indicated that many of them release small amounts of nitrosamines.[1] However, nitrosamines from condoms are not expected to be of toxicological significance.[3]
Cancer
In 1956, two British scientists, John Barnes and Peter Magee, reported that dimethylnitrosamine produced liver tumours in rats. Research was undertaken and around 90% of nitrosamine compounds were deemed to be carcinogenic.[4]
In the 1970s, there was an increased frequency of liver cancer found in Norwegian farm animals. The farm animals had been fed on herring meal, which was preserved using sodium nitrite. The sodium nitrite had reacted with dimethylamine in the fish and produced dimethylnitrosamine.[4]
Nitrosamines can cause cancers in a wide variety of animal species, a feature that suggests that they may also be carcinogenic in humans. Epidemiological data supports a positive association between nitrite and nitrosamine intake and gastric cancer, between meat and processed meat intake and gastric cancer and oesophageal cancer, but the studies are inconclusive.[5]
Examples of nitrosamines
| Substance Name | CAS # | Synonyms | Molecular Formula | Physical Appearance | Found in | Sources | Carcinogenicity Category |
|---|---|---|---|---|---|---|---|
| N-Nitrosonornicotine | NNN | C9H11N3O | Tobacco smoke | ||||
| 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone | NNK; 4'-(nitrosomethylamino)-1-(3-pyridyl)-1-butanone | C10H13N3O2 | Tobacco smoke | [6] | |||
| 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol | 76014-81-8 | NNAL | Tobacco smoke | ||||
| N-Nitrosoanabasine | 37620-20-5 | NAB | Tobacco smoke | IARC-3 | |||
| N-Nitrosoanatabine | 71267-22-6 | IARC-3 | |||||
| 4-(Methylnitrosoamino)-4-(3-pyridyl)-1-butanol | Iso-NNAL | Tobacco smoke | |||||
| 4-(N-Methylnitrosamino)-4-(3-pyridyl)butyric acid | Iso-NNAC | Tobacco smoke | |||||
| N-Nitrosodiethylamine | 55-18-5 | diethylnitrosamide, diethylnitrosamine, N,N-diethylnitrosamine, N-ethyl-N-nitrosoethanamine, diethylnitrosamine, DANA, DENA, DEN, NDEA | C4H10N2O | yellow liquid | [7] [8] [9] | EPA-B2; IARC-2A | |
| N-Nitrosodimethylamine | 62-75-9 | Dimethylnitrosamine, N,N-Dimethylnitrosamine, NDMA | C2H6N2O | EPA-B2; IARC-2A; OSHA Carcinogen; TLV-A3 | |||
| 2-Nitro-p-phenylenediamine | 5307-14-2 | IARC-3 | |||||
| N-Nitrosodi-n-butylamide | 924-16-3 | DBN | EPA-B2; IARC-2B | ||||
| N-Nitrosodiethanolamine | 1116-54-7 | NDELA | EPA-B2; IARC-2B | ||||
| N-Nitrosodiphenylamine | 86-30-6 | IARC-3 | |||||
| p-Nitrosodiphenylamine | 156-10-5 | IARC-3 | |||||
| N-Nitrosodi-n-propylamine | 621-64-7 | NDPA | EPA-B2, IARC-2B | ||||
| N-Nitrosoethylphenylamine | 612-64-6 | ||||||
| N-Nitrosomethylphenylamine | 614-00-6 | ||||||
| 2-Nitrodiphenylamine | 119-75-5 | NDPA, 2-NDPA, 2NO2DPA, Sudan Yellow 1339, C.I. 10335, CI 10335, phenyl 2-nitrophenylamine, 2-nitro-N-phenylaniline,N-phenyl-o-nitroaniline | C12H10N2O2 | red crystalline solid | stabilizer of synthetic rubber |
See also
- Nitroamine (without the 's'), compounds of the formula R2N-NO2.
- Nitroso, compounds of the formula R-NO
References
- ^ Mulliken, Samuel Parsons "A method for the identification of pure organic compounds" John Wiley & Sons; 1916; 327 pages
- ^ Gregory N. Connolly, and Howard Saxner (August 21, 2001). "Informational Update Research on Tobacco Specific Nitrosamines (TSNAs) in Oral Snuff and a Request to Tobacco Manufacturers to Voluntarily Set Tolerance Limits For TSNAs in Oral Snuff" (PDF).
{{cite journal}}: Cite journal requires|journal=(help) - ^ Proksch E. Toxicological evaluation of nitrosamines in condoms. Int J Hyg Environ Health. 2001 Nov;204(2-3):103-10. PMID 11759152
- ^ a b ""Nitrosamines and Cancer"". Retrieved 2009-09-06.
- ^ Jakszyn P, Gonzalez CA. Nitrosamine and related food intake and gastric and oesophageal cancer risk: a systematic review of the epidemiological evidence. World J Gastroenterol. 2006 Jul 21;12(27):4296-303. PMID 16865769
- ^ Hecht, Steven S.; Borukhova, Anna; Carmella, Steven G. "Tobacco specific nitrosamines" Chapter 7; of "Nicotine safety and toxicity" Society for Research on Nicotine and Tobacco; 1998 - 203 pages
- ^ NIH Substance Profile
- ^ Spectrum; Chemical Fact Sheet
- ^ Safety data for N-nitrosodiethylamine