Structure of the nitrosamino group

Nitrosamines are chemical compounds of the chemical structure R₁N(-R₂)-N=O, some of which are carcinogenic. Image File history File links Download high-resolution version (1163x1085, 13 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Nitrosamine ... Image File history File links Download high-resolution version (1163x1085, 13 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Nitrosamine ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... Chemical structure refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. ... Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ...

Occurrence 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. // Definition The nitrite ion is NO2−. A nitrite compound is one that contains this group, either an ionic compound, or an analogous covalent one. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... For other uses, see Acid (disambiguation). ... In anatomy, the stomach is a bean-shaped hollow muscular organ of the gastrointestinal tract involved in the second phase of digestion, following mastication. ...

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. Nitrous acid (molecular formula HNO2) is a weak monobasic acid known only in solution and in the form of nitrite salts. ... The structure of the nitrosonium ion The nitrosonium ion is NO+, the nitrogen atom is bonded to an oxygen atom with a bond order of 2, the overall diatomic species bearing a positive charge. ... A cation is an ion with positive charge. ... Hydroxide is a polyatomic ion consisting of oxygen and hydrogen: OH− It has a charge of −1. ... An anion is an ion with negative charge. ...

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 enhance nitrosamine formation. For other uses, see Beer (disambiguation). ... For other uses, see Fish (disambiguation). ... Kinnikuman character, see Meat Alexandria. ... Cheese is a solid food made from the milk of cows, goats, sheep, and other mammals. ... This article deals with the molecular aspects of ascorbic acid. ...

Occurrence 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] Shredded tobacco leaf for pipe smoking Tobacco can also be pressed into plugs and sliced into flakes Tobacco is an agricultural product processed from the fresh leaves of plants in genus Nicotiana. ... For other uses, see latex (disambiguation). ... Balloons, like greeting cards or flowers, are given for special occasions. ... A condom is a device, usually made of latex, or more recently polyurethane, that is used during sexual intercourse. ... Toxicology (from the Greek words toxicos and logos [1]) is the study of the adverse effects of chemicals on living organisms [2]. It is the study of symptoms, mechanisms, treatments and detection of poisoning, especially the poisoning of people. ...

Cancer

Nitrosamines can cause cancers in a wide variety of animal species, a feature which suggests that they may also be carcinogenic in humans. Epidemiological data suggests that nitrosamines in preserved food cause stomach cancer.^[2] Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ...

Uses^{[citation needed]}

• Rubber products
• Pesticides
• Certain cosmetics

Examples of nitrosamines

Tobacco-specific nitrosamines

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

N-Nitrosonornicotine (abbreviated NNN) is a nitrosamine found in tobacco that has been classified by the IARC as a Group 2B carcinogen. ... 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (abbreviated NNK) is a nitrosamine present in tobacco that is a potent procarcinogen. ...

Other nitrosamines

• NDEA
• NDMA

The National Defense Education Act (NDEA) is a United States Act of Congress, passed in 1958 providing aid to education in the United States at all levels, both public and private. ... N-nitrosodidimethylamine (NDMA) ia a volatile N-nitrosamine (VNA) and a known carcinogen of animals and possibly of humans. ...

See also

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

Nitroamines are organic compounds that contain the chemical group R2N-NO2. ... Nitroso refers to a functional group in organic chemistry which has the general formula R-NO. Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines. ...

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

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