Nitrosamine

Not to be confused with Nitroamine.

Nitrosamines (or more formally N-nitrosamines) are organic compounds produced by industrial processes.[1]

The chemical structure is R2N−N=O, where R is usually an alkyl group.[2] Nitrosamines have a nitroso group (NO+) that are "probable human carcinogens",[3] bonded to a deprotonated amine. Most nitrosamines are carcinogenic in animals.[4] A 2006 systematic review supports a "positive association between nitrite and nitrosamine intake and gastric cancer, between meat and processed meat intake and gastric cancer and oesophageal cancer, and between preserved fish, vegetable and smoked food intake and gastric cancer, but is not conclusive".[5]

  1. ^ California Water Boards, State Water Resources Control Board, "Nitrosamines", 09 December 2024
  2. ^ Beard, Jessica C.; Swager, Timothy M. (21 January 2021). "An Organic Chemist's Guide to N-Nitrosamines: Their Structure, Reactivity, and Role as Contaminants". The Journal of Organic Chemistry. 86 (3): 2037–2057. doi:10.1021/acs.joc.0c02774. PMC 7885798. PMID 33474939.
  3. ^ World Health Organization, Medical product alert, Note on Nitrosamine impurities, "Update on Nitrosamine impurities", 20 November 2019
  4. ^ Yang, Chung S.; Yoo, Jeong-Sook H.; Ishizaki, Hiroyuki; Hong, Junyan (1990). "Cytochrome P450IIe1: Roles in Nitrosamine Metabolism and Mechanisms of Regulation". Drug Metabolism Reviews. 22 (2–3): 147–159. doi:10.3109/03602539009041082. PMID 2272285.
  5. ^ Jakszyn, Paula; Gonzalez, Carlos (2006). "Nitrosamine and related food intake and gastric and oesophageal cancer risk: A systematic review of the epidemiological evidence". World Journal of Gastroenterology. 12 (27): 4296–4303. doi:10.3748/wjg.v12.i27.4296. PMC 4087738. PMID 16865769.
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