亞硝胺
外觀
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。
用途
[編輯]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;
環三亞甲基三亞硝胺(Trimethylenetrinitrosamine;R鹽)為RDX的中間體之一,二戰期間曾用作軍用炸藥。
分佈
[編輯]亞硝胺在橡膠製品、食品和其他消費品中均有分佈[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、口含煙及嗅煙(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]。
致突變性
[編輯]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學調查表明,攝入亞硝胺與胃癌、食道癌的發生有着正相關性,但尚無證據直接證實亞硝胺的致癌性質。[10]
代表成員
[編輯]名稱 | CAS號 | 別名 | 分子式 | 外觀 | 致癌性分級 |
---|---|---|---|---|---|
N-亞硝基降煙鹼 | 16543-55-8 | NNN | C9H11N3O | 淡黃色固體,熔點低 | |
4-甲基亞硝胺基-1-3-吡啶基-1-丁酮[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-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-亞硝基新煙草鹼 | 37620-20-5 | NAB | C10H13N3O | 黃色油狀液體 | IARC-3 |
N-亞硝基新煙鹼 | 71267-22-6 | NAT | C10H11N3O | 黃色至橙色的清澈液體 | IARC-3 |
參見
[編輯]參考資料
[編輯]- ^ 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.
- ^ 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.
- ^ Vogel, A. I. Practical Organic Chemistry 3rd. Impression. 1962: 1074.
- ^ Vogel, A. I. Practical Organic Chemistry 3rd. Impression. 1962: 649.
- ^ Glagovich, Neil. The Libermann Nitroso Reaction. Connecticut State University. [28 December 2015]. (原始內容存檔於2013-03-05).
- ^ 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.
- ^ Scanlan, Dr. Richard A. Nitrosamines and Cancer. Nitrosamines and Cancer. The Linus Pauling Institute. 22 April 2000 [28 December 2015]. (原始內容存檔於2015-12-28).
- ^ 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.
- ^ E-cigarettes: harmless inhaled or exhaled, No second hand smoke. Health New Zealand. [27 June 2014]. (原始內容存檔於2016-04-25).
- ^ 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.
- ^ 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
- ^ [ NIH Substance Profile]
- ^ [ Spectrum; Chemical Fact Sheet]
- ^ [ Safety data for N-nitrosodiethylamine]