Nitrosamine

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Nitrosamines are chemical compounds of the chemical structure R₁N(-R₂)-N=O, some of which are carcinogenic.

Contents 1 Occurence in food 2 Occurence in other consumer products 3 Cancer 4 Uses[citation needed] 5 Examples of nitrosamines 5.1 Tobacco-specific nitrosamines 5.2 Other nitrosamines 6 See also 7 External links 8 References

[edit] Occurence in 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.

The nitrite forms nitrous acid (HNO₂), which splits into the nitrosonium cation, N=O⁺, and the hydroxide anion, OH⁻. The nitrosonium cation then reacts with an amine to produce nitrosamine.

Nitrosamines are found in many foodstuffs especially beer, fish, fish byproducts, and in meat and cheese products preserved with nitrite pickling salt. The US government established limits on the amount of nitrites used in meat products 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.

[edit] Occurence in other consumer products

Nitrosamines can be found in tobacco smoke and 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.^[1]

[edit] Cancer

Nitrosamines can cause cancers in a wide variety of animal species, a feature which suggests that they may also be carcinogenic in humans. Subtle changes in the structure of nitrosamines produce cancer in various organs^{[citation needed]}. Epidemiological data suggests that nitrosamines in preserved food causes stomach cancer.^[2]

[edit] Uses^{[citation needed]}

• Rubber products
• Pesticides
• Certain cosmetics

[edit] Examples of nitrosamines

[edit] Tobacco-specific nitrosamines

• N-Nitrosonornicotine (NNN)
• NNK
• NNAL
• NAT
• NAB
• iso-NNAL
• iso-NNAC

[edit] Other nitrosamines

• NDEA
• NDMA

[edit] See also

• Nitroamine (without the 's'), compounds of the formula R₂N-NO₂.
• Nitroso, compounds of the formula R-NO

[edit] External links

• Oregon State University, Linus Pauling Institute article on Nitrosamines and cancer, including info on history of meat laws
• Risk factors in Pancreatic Cancer

[edit] References

1. ^ Proksch E. Toxicological evaluation of nitrosamines in condoms. Int J Hyg Environ Health. 2001 Nov;204(2-3):103-10. PubMed
2. ^ 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. PubMed