亚硝胺

亚硝胺（英语：Nitrosamine）（不可称为亚硝酸胺）是一类通式为R¹N(–R²)–N=O的胺化合物，其大部分成员都属强致癌物。

亚硝胺广泛应用于化妆品、杀虫剂与树脂的生产。

其中N,N'-二亚硝基五亚甲基四胺（N,N'-Dinitrosopentamethylenetetramine；发泡剂H）是一种重要的胶乳发泡剂；

环三亚甲基三亚硝胺（Trimethylenetrinitrosamine；R盐）为RDX的中间体之一，二战期间曾用作军用炸药。

亚硝胺在橡胶制品、食品和其他消费品中均有分布^[1]。有研究预计避孕套中的亚硝胺没有毒理学意义。^[2]

在酸性环境（如消化液）中，食物中的亚硝酸盐发生质子化而产生亚硝酰阳离子N≡O⁺与水：

H
2NO+
2 → H₂O + NO⁺.

N≡O⁺随即与胺（包括蛋白质及其降解产物）反应而生成亚硝胺^[3] ；油煎、烧烤的高温对此特别有促进作用。

Liebermann反应（英语：Liebermann nitroso reaction）能够提示亚硝胺的存在^[4]。若检测结果呈阴性，则试剂显红色或兰色（苯酚存在时）。^[5]

因亚硝化/亚硝解反应的存在，肉类、泡菜、奶酪等富含亚硝酸盐的食品中亚硝胺浓度水平极高。美国政府对肉制品亚硝酸盐含量实行严格规制，旨在降低公民罹患癌症的风险^[6]。为抑制亚硝胺的生成，抗坏血酸或其衍生物被要求添加到肉制品中^[7]。

包括鼻烟油、口含烟及嗅烟（尽管含量较前二者低）的烟草制品均含有亚硝胺^[8]。电子烟生产中丙二醇的使用亦可引入痕量亚硝胺^[9]。

动物实验已证实某些亚硝胺具有明显的致癌性，并提示其对人可能也有致癌作用。基于对照实验的流行病学调查表明，摄入亚硝胺与胃癌、食道癌的发生有着正相关性，但尚无证据直接证实亚硝胺的致癌性质。^[10]

More information 名称, CAS号 ...

名称	CAS号	别名	分子式	外观	致癌性分级
N-亚硝基降烟碱	16543-55-8	NNN	C₉H₁₁N₃O	淡黄色固体，熔点低
4-甲基亚硝胺基-1-3-吡啶基-1-丁酮（英语：NNK）^[11]	64091-91-4	NNK, 4′-(nitrosomethylamino)-1-(3-pyridyl)-1-butanone	C₁₀H₁₅N₃O₂	浅黄色油状液体
N-亚硝基二甲胺	62-75-9	Dimethylnitrosamine, N,N-dimethylnitrosamine, NDMA, DMN	C₂H₆N₂O	黄色液体	EPA-B2; IARC-2A; OSHA carcinogen; TLV（英语：Threshold Limit Value）-A3
N-亚硝基二乙胺^[12]^[13]^[14]	55-18-5	Diethylnitrosamide, diethylnitrosamine, N,N-diethylnitrosamine, N-ethyl-N-nitrosoethanamine, diethylnitrosamine, DANA, DENA, DEN, NDEA	C₄H₁₀N₂O	黄色液体	EPA-B2; IARC-2A
4-(甲基亚硝胺)-1-(3-吡啶基)-1-丙醇	76014-81-8	NNAL
N-亚硝基新烟草碱	37620-20-5	NAB	C₁₀H₁₃N₃O	黄色油状液体	IARC-3
N-亚硝基新烟碱	71267-22-6	NAT	C₁₀H₁₁N₃O	黄色至橙色的清澈液体	IARC-3

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[1]
Altkofer, W; Braune, S; Ellendt, K; Kettl-Grömminger, M; Steiner, G. Migration of nitrosamines from rubber products--are balloons and condoms harmful to the human health?. Molecular nutrition & food research. 2005, 49 (3): 235–8. PMID 15672455. doi:10.1002/mnfr.200400050.
[2]
Proksch, E. Toxicological evaluation of nitrosamines in condoms. International journal of hygiene and environmental health. 2001, 204 (2–3): 103–10. PMID 11759152. doi:10.1078/1438-4639-00087.
[3]
Vogel, A. I. Practical Organic Chemistry 3rd. Impression. 1962: 1074.
[4]
Vogel, A. I. Practical Organic Chemistry 3rd. Impression. 1962: 649.
[5]
Glagovich, Neil. The Libermann Nitroso Reaction. Connecticut State University. [28 December 2015]. （原始内容存档于2013-03-05）.
[6]
Honikel, Karl-Otto. The use and control of nitrate and nitrite for the processing of meat products. Meat Science. January–February 2008, 78: 68–76. doi:10.1016/j.meatsci.2007.05.030.
[7]
Scanlan, Dr. Richard A. Nitrosamines and Cancer. Nitrosamines and Cancer. The Linus Pauling Institute. 22 April 2000 [28 December 2015]. （原始内容存档于2015-12-28）.
[8]
Gregory N. Connolly, and Howard Saxner. 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. August 21, 2001.
[9]
E-cigarettes: harmless inhaled or exhaled, No second hand smoke. Health New Zealand. [27 June 2014]. （原始内容存档于2016-04-25）.
[10]
Jakszyn, P; Gonzalez, CA. Nitrosamine and related food intake and gastric and oesophageal cancer risk: A systematic review of the epidemiological evidence. World journal of gastroenterology : WJG. 2006, 12 (27): 4296–303. PMC 4087738 . PMID 16865769.
[11]
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
[12]
[ NIH Substance Profile]
[13]
[ Spectrum; Chemical Fact Sheet]
[14]
[ Safety data for N-nitrosodiethylamine]

[1] [1]
Altkofer, W; Braune, S; Ellendt, K; Kettl-Grömminger, M; Steiner, G. Migration of nitrosamines from rubber products--are balloons and condoms harmful to the human health?. Molecular nutrition & food research. 2005, 49 (3): 235–8. PMID 15672455. doi:10.1002/mnfr.200400050.

[2] [2]
Proksch, E. Toxicological evaluation of nitrosamines in condoms. International journal of hygiene and environmental health. 2001, 204 (2–3): 103–10. PMID 11759152. doi:10.1078/1438-4639-00087.

[3] [3]
Vogel, A. I. Practical Organic Chemistry 3rd. Impression. 1962: 1074.

[4] [4]
Vogel, A. I. Practical Organic Chemistry 3rd. Impression. 1962: 649.

[5] [5]
Glagovich, Neil. The Libermann Nitroso Reaction. Connecticut State University. [28 December 2015]. （原始内容存档于2013-03-05）.

[6] [6]
Honikel, Karl-Otto. The use and control of nitrate and nitrite for the processing of meat products. Meat Science. January–February 2008, 78: 68–76. doi:10.1016/j.meatsci.2007.05.030.

[7] [7]
Scanlan, Dr. Richard A. Nitrosamines and Cancer. Nitrosamines and Cancer. The Linus Pauling Institute. 22 April 2000 [28 December 2015]. （原始内容存档于2015-12-28）.

[8] [8]
Gregory N. Connolly, and Howard Saxner. 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. August 21, 2001.

[9] [9]
E-cigarettes: harmless inhaled or exhaled, No second hand smoke. Health New Zealand. [27 June 2014]. （原始内容存档于2016-04-25）.

[10] [10]
Jakszyn, P; Gonzalez, CA. Nitrosamine and related food intake and gastric and oesophageal cancer risk: A systematic review of the epidemiological evidence. World journal of gastroenterology : WJG. 2006, 12 (27): 4296–303. PMC 4087738 . PMID 16865769.

[11] [11]
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

[12] [12]
[ NIH Substance Profile]

[13] [13]
[ Spectrum; Chemical Fact Sheet]

[14] [14]
[ Safety data for N-nitrosodiethylamine]

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亚硝胺

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用途

分布

致突变性

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