Nitrosamine

Nitrosamine
Not to be confused with nitroamine.
Structure of the nitrosamino group

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

Contents

Usages

Nitrosamines are used in manufacture of some cosmetics, pesticides, and in most rubber products.[citation needed]

Occurrences

Nitrosamine occurs in latex products such as balloons,[1] and in many foods and other consumables. Nitrosamines from condoms are not expected to be of toxicological significance.[2]

In foods, 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.[3]

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.[4]

These processes lead to significant levels of nitrosamines 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]

Nitrosamines can also 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.)[5]

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.[6]

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.[6]

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."[7]

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

Examples of nitrosamines

Main article: Tobacco-specific 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[8] 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[9][10][11] 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

See also

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

References

  1. ^ Altkofer, W; Braune, S; Ellendt, K; Kettl-Grömminger, M; Steiner, G (2005). "Migration of nitrosamines from rubber products--are balloons and condoms harmful to the human health?". Molecular nutrition & food research 49 (3): 235–8. doi:10.1002/mnfr.200400050. PMID 15672455. 
  2. ^ Proksch, E (2001). "Toxicological evaluation of nitrosamines in condoms". International journal of hygiene and environmental health 204 (2–3): 103–10. PMID 11759152. 
  3. ^ Mulliken, Samuel Parsons "A method for the identification of pure organic compounds" John Wiley & Sons; 1916; 327 pages
  4. ^ Vogel A I, Practical Organic Chemistry, 3rd Ed. Impression 1962 p. 1074
  5. ^ 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. http://smallbusiness.findlaw.com/finances-taxes/news/hdocs/docs/tobacco/masnuffsstudy.pdf. 
  6. ^ a b "Nitrosamines and Cancer". http://lpi.oregonstate.edu/f-w00/nitrosamine.html. Retrieved 2009-09-06. 
  7. ^ 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
  8. ^ 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
  9. ^ NIH Substance Profile
  10. ^ Spectrum; Chemical Fact Sheet
  11. ^ Safety data for N-nitrosodiethylamine

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  • Nitrosamīne — entstehen durch Einwirkung von salpetriger Säure auf sekundäre Amine und bilden meist ölige, gelbliche Flüssigkeiten von gewürzigem Geruch, unlöslich in Wasser und unzersetzt destillierbar. Sie liefern mit Zinkstaub und Essigsäure sekundäre… …   Meyers Großes Konversations-Lexikon

  • nitrosamine — ● nitrosamine nom féminin Amide de l acide nitreux, de formule générale R′RN―NO …   Encyclopédie Universelle

  • nitrosamine — [nī΄trōs am′ēn΄, nī΄trōs am′in; nī trōs′ə mēn΄] n. [< NITROSO + AMINE] any of a series of organic compounds derived from amines and containing the N·NO group: they are found in foods, herbicides, and industrial products and are formed in the… …   English World dictionary

  • Nitrosamine — Allgemeine Formel der Nitrosamine. Sind R1 und R2 Organylreste, sind die Nitrosamine stabiler als wenn R1 oder R2 für ein Wasserstoffatom stehen. Nitrosamine, genauer N Nitrosamine, sind eine Stoffklasse organisch chemischer Verbindungen der… …   Deutsch Wikipedia

  • Nitrosamine — ◆ Ni|tros|a|mi|ne auch: Ni|tro|sa|mi|ne 〈Pl.; Chem.〉 durch Reaktion mit Salpetersäure entstandene Amine, die im Verdacht stehen, krebserregend zu sein [<Nitro... + Amin] ◆ Die Buchstabenfolge ni|tr... kann in Fremdwörtern auch nit|r...… …   Universal-Lexikon

  • nitrosamine — /ˌnaɪtroʊsəˈmin/ (say .nuytrohsuh meen), /naɪtroʊsˈæmən/ (say nuytrohs amuhn) noun any of a series of oily compounds with the type formula R2NNO. Also, nitrosamin /naɪtroʊsˈæmən/ (say nuytrohs amuhn). {German Nitrosamine; nitros(o) + amine} …  

  • nitrosamine — noun Date: 1878 any of various organic compounds which are characterized by the grouping NNO and some of which are powerful carcinogens …   New Collegiate Dictionary

  • nitrosamine — /nuy troh seuh meen , nuy trohs am in/, n. Chem. any of a series of compounds with the type formula R2NNO, some of which are carcinogenic, formed in cured meats by the conversion of nitrite. [1875 80; NITROS + AMINE] * * * …   Universalium

  • nitrosamine — noun a) a divalent functional group, >N.N=O b) any of a class of organic compounds containing this group; prepared by the reaction of amines with nitrites; they are carcinogenic …   Wiktionary

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