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Nitrosamine information


Structure of the nitrosamino group

In organic chemistry, nitrosamines (or more formally N-nitrosamines) are organic compounds with the chemical structure R2N−N=O, where R is usually an alkyl group.[1] They feature a nitroso group (NO+) bonded to a deprotonated amine. Most nitrosamines are carcinogenic in nonhuman animals.[2] 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".[3]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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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Nitrosamine

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growth of bacteria that facilitate the formation of tobacco-specific nitrosamines, while preserving the desired texture and mouthfeel of the snus. The...

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In biochemistry, nitrosamines are a class of compounds that can form during food digestion. The presence of their precursors, nitrites, in cured meats...

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Pancetta

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risk is likely related to the presence of nitrosamines in processed meat products like pancetta. Nitrosamines are carcinogenic compounds formed by the...

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Bacon

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the formation of nitrosamines but has no effect on S-Nitrosothiols and nitrosyl-heme. Vitamin E (tocopherol) also reduces nitrosamine levels. Bacon fried...

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Diazonium compound

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implicated as the causative agents in the carcinogens. Specifically, nitrosamines are thought to undergo metabolic activation to produce alkanediazonium...

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that class of products (e.g., low nitrosamine Swedish-type snus versus other smokeless tobacco with high nitrosamine levels). It is estimated the safety...

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2 H+ → NO+ + H2O R2NH + NO+ → R2N-NO + H+ Formation of an N-nitrosamine: The nitrosamine can then lose water through protonation to form diazonium cation...

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Ranitidine

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presence of nitrosamine impurities and asked them to review all chemical and biological human medicines for the presence of nitrosamines and to test the...

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one API producer. Since then, FDA has determined that other types of nitrosamine compounds, e.g., N-Nitrosodiethylamine (NDEA), are present at unacceptable...

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Losartan

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ongoing investigation into ARB drug products; reports on finding of a new nitrosamine impurity in certain lots of losartan and product recall" (Press release)...

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Beetroot

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the anus, usually in or with stool) or hematuria (blood in the urine). Nitrosamine formation in beetroot juice can reliably be prevented by adding ascorbic...

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Alkyl nitrite

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sulfonamides n-Butyl nitrite and ammonia convert phenylhydroxylamine to its nitrosamine derivative cupferron. Likewise pyrrolidine is a substrate for ethyl nitrite...

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Charcuterie

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effects are presumed to be caused by nitrates and nitrites, as well as nitrosamines which are formed by nitrites reacting with meat. These risks are generally...

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Rifampicin

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August 2020, the U.S. Food and Drug Administration (FDA) became aware of nitrosamine impurities in certain samples of rifampin. The FDA and manufacturers...

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Cooking

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by reducing the time needed for the meat to be cooked at high heat. Nitrosamines are found in some food, and may be produced by some cooking processes...

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Nitrate

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mouth. Nitrites lead to the formation of carcinogenic nitrosamines. The production of nitrosamines may be inhibited by the use of the antioxidants vitamin...

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Valsartan

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guidance to marketing authorization holders on how to avoid the presence of nitrosamine impurities in human medicines and asked them to review all chemical and...

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Sodium nitrite

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(vitamin E) to further inhibit nitrosamine production. α-Tocopherol, ascorbic acid, and erythorbic acid all inhibit nitrosamine production by their oxidation-reduction...

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Sildenafil

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S-Nitrosoglutathione (GSNO, SNOG) SNO-t-PA SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black...

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