Nitrosamine

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

Contents 1 Usages 2 Occurrences 2.1 Food 2.2 Consumer products 3 Cancer 4 Examples of nitrosamines 5 See also 6 References 7 External links

[edit] Usages

• Most rubber products
• Pesticides
• Certain cosmetics

[edit] Occurrences

[edit] 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 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. .^{[citation needed]} There are also rules about adding ascorbic acid or related compounds to meat, in order to inhibit nitrosamine formation.^{[citation needed]}

[edit] 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]

[edit] Cancer

In 1956, two British scientists, John Barnes and Peter Magee, reported that dimethylnitrosamine produced liver tumours in rats. Research was undertaken and approximately 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. "At present, available epidemiological evidence from case-control studies on nitrite and nitrosamine intake supports a positive association with gastric cancer risk. The evidence in relation with oesophageal cancer is insufficient."^[5]

Hydrazines derived from these Nitrosamines, e.g. UDMH, are also carcinogenic.

[edit] Examples of nitrosamines

Substance Name	CAS #	Synonyms	Molecular Formula	Physical Appearance	Carcinogenicity Category
N-Nitrosonornicotine	16543-55-8	NNN	C9H11N3O	Oily yellow liquid
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone[6]	64091-91-4	NNK, 4'-(nitrosomethylamino)-1-(3-pyridyl)-1-butanone	C10H13N3O2
N-Nitrosodimethylamine	62-75-9	Dimethylnitrosamine, N,N-Dimethylnitrosamine, NDMA, DMN	C2H6N2O	Yellow liquid	EPA-B2; IARC-2A; OSHA Carcinogen; TLV-A3
N-Nitrosodiethylamine[7][8][9]	55-18-5	diethylnitrosamide, diethylnitrosamine, N,N-diethylnitrosamine, N-ethyl-N-nitrosoethanamine, diethylnitrosamine, DANA, DENA, DEN, NDEA	C4H10N2O	Yellow liquid	EPA-B2; IARC-2A
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol]	76014-81-8	NNAL
N-Nitrosoanabasine	37620-20-5	NAB			IARC-3
N-Nitrosoanatabine	71267-22-6				IARC-3

[edit] See also

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

[edit] References

[edit] External links