亚硝胺

亞硝胺（英語：Nitrosamine）（不可稱為亞硝酸胺）是一類通式為R¹N(–R²)–N=O的胺化合物，其大部分成員都屬強致癌物。

亞硝胺廣泛應用於化妝品、殺蟲劑與樹脂的生產。

其中N,N'-二亞硝基五亞甲基四胺（N,N'-Dinitrosopentamethylenetetramine；發泡劑H）是一種重要的膠乳發泡劑；

环三亚甲基三亚硝胺（Trimethylenetrinitrosamine；R鹽）為RDX的中間體之一，二戰期間曾用作軍用炸藥。

亞硝胺在橡膠製品、食品和其他消費品中均有分布^[1]。有研究預計避孕套中的亞硝胺沒有毒理學意義。^[2]

在酸性環境（如消化液）中，食物中的亞硝酸鹽發生質子化而產生亞硝酰陽離子N≡O⁺與水：

H
2NO+
2 → H₂O + NO⁺.

N≡O⁺隨即與胺（包括蛋白質及其降解產物）反應而生成亞硝胺^[3] ；油煎、燒烤的高溫對此特別有促進作用。

Liebermann反應（英语：Liebermann nitroso reaction）能夠提示亞硝胺的存在^[4]。若檢測結果呈陰性，則試劑顯紅色或蘭色（苯酚存在時）。^[5]

因亞硝化/亞硝解反應的存在，肉類、泡菜、奶酪等富含亞硝酸鹽的食品中亞硝胺濃度水平極高。美國政府對肉製品亞硝酸鹽含量實行嚴格規制，旨在降低公民罹患癌症的風險^[6]。為抑製亞硝胺的生成，抗壞血酸或其衍生物被要求添加到肉製品中^[7]。

包括鼻煙油、口含烟及嗅煙（儘管含量較前二者低）的煙草製品均含有亞硝胺^[8]。電子煙生產中丙二醇的使用亦可引入痕量亞硝胺^[9]。

動物實驗已證實某些亞硝胺具有明顯的致癌性，並提示其對人可能也有致癌作用。基於對照實驗的流行病学调查表明，攝入亞硝胺與胃癌、食道癌的發生有著正相關性，但尚無證據直接證實亞硝胺的致癌性質。^[10]

更多信息 名稱, CAS号 ...

名稱	CAS号	別名	分子式	外觀	致癌性分級
N-亞硝基降菸鹼	16543-55-8	NNN	C₉H₁₁N₃O	淡黃色固體，熔點低
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	淺黃色油狀液體
N-亞硝基二甲胺	62-75-9	Dimethylnitrosamine, N,N-dimethylnitrosamine, NDMA, DMN	C₂H₆N₂O	黃色液體	EPA-B2; IARC-2A; OSHA carcinogen; TLV（英语：Threshold Limit Value）-A3
N-亞硝基二乙胺^[12]^[13]^[14]	55-18-5	Diethylnitrosamide, diethylnitrosamine, N,N-diethylnitrosamine, N-ethyl-N-nitrosoethanamine, diethylnitrosamine, DANA, DENA, DEN, NDEA	C₄H₁₀N₂O	黃色液體	EPA-B2; IARC-2A
4-(甲基亞硝胺)-1-(3-吡啶基)-1-丙醇	76014-81-8	NNAL
N-亞硝基新菸草鹼	37620-20-5	NAB	C₁₀H₁₃N₃O	黃色油狀液體	IARC-3
N-亞硝基新菸鹼	71267-22-6	NAT	C₁₀H₁₁N₃O	黃色至橙色的清澈液體	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]

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[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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[3]

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亚硝胺

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亚硝胺

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