• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

有机化学家的亚硝胺指南:其结构、反应性及作为污染物的作用

An Organic Chemist's Guide to -Nitrosamines: Their Structure, Reactivity, and Role as Contaminants.

作者信息

Beard Jessica C, Swager Timothy M

机构信息

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

出版信息

J Org Chem. 2021 Feb 5;86(3):2037-2057. doi: 10.1021/acs.joc.0c02774. Epub 2021 Jan 21.

DOI:10.1021/acs.joc.0c02774
PMID:33474939
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7885798/
Abstract

-Nitrosamines are a class of compounds notorious both for the potent carcinogenicity of many of its members and for their widespread occurrence throughout the human environment, from air and water to our diets and drugs. Considerable effort has been dedicated to understanding -nitrosamines as contaminants, and methods for their prevention, remediation, and detection are ongoing challenges. Understanding the chemistry of -nitrosamines will be key to addressing these challenges. To facilitate such understanding, we focus in this Perspective on the structure, reactivity, and synthetic applications of -nitrosamines with an emphasis on alkyl -nitrosamines. The role of -nitrosamines as water contaminants and the methods for their detection are also discussed.

摘要

亚硝胺是一类化合物,因其许多成员具有强大的致癌性以及在人类环境中广泛存在而声名狼藉,从空气、水到我们的饮食和药物。人们已经投入了大量精力来了解亚硝胺作为污染物的情况,其预防、修复和检测方法仍然是持续面临的挑战。了解亚硝胺的化学性质将是应对这些挑战的关键。为了促进这种理解,我们在本综述中重点关注亚硝胺的结构、反应性和合成应用,尤其侧重于烷基亚硝胺。还讨论了亚硝胺作为水污染物的作用及其检测方法。

相似文献

1
An Organic Chemist's Guide to -Nitrosamines: Their Structure, Reactivity, and Role as Contaminants.有机化学家的亚硝胺指南:其结构、反应性及作为污染物的作用
J Org Chem. 2021 Feb 5;86(3):2037-2057. doi: 10.1021/acs.joc.0c02774. Epub 2021 Jan 21.
2
Comparison of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry with electron ionization for determination of N-nitrosamines in environmental water.比较气相色谱-质谱法和气相色谱-串联质谱法与电子电离法测定环境水中的亚硝胺。
Chemosphere. 2017 Feb;168:1400-1410. doi: 10.1016/j.chemosphere.2016.11.109. Epub 2016 Dec 5.
3
Seasonal occurrence of N-nitrosamines and their association with dissolved organic matter in full-scale drinking water systems: Determination by LC-MS and EEM-PARAFAC.规模化饮用水系统中 N-亚硝胺的季节性出现及其与溶解有机物的关系:通过 LC-MS 和 EEM-PARAFAC 的测定。
Water Res. 2020 Sep 15;183:116096. doi: 10.1016/j.watres.2020.116096. Epub 2020 Jun 22.
4
Metabolic fate of N-alkyl-N-(3-hydroxypropyl and 2-hydroxy-ethyl)nitrosamines in the rat in relation to the induction of bladder cancer by N-butyl-N-(4-hydroxybutyl)nitrosamine and its homologs.大鼠体内N-烷基-N-(3-羟丙基和2-羟乙基)亚硝胺的代谢命运与N-丁基-N-(4-羟丁基)亚硝胺及其同系物诱发膀胱癌的关系。
Gan. 1981 Apr;72(2):254-8.
5
Metabolic fate and carcinogenicity of N-(omega-hydroxyalkyl) N-(4-hydroxybutyl) nitrosamines analogs of N-butyl-N-(4-hydroxy-butyl) nitrosamine, in the rat.大鼠体内N-丁基-N-(4-羟丁基)亚硝胺的N-(ω-羟烷基)N-(4-羟丁基)亚硝胺类似物的代谢命运和致癌性
Gan. 1981 Aug;72(4):539-46.
6
Ruthenium Catalysts for the Reduction of N-Nitrosamine Water Contaminants.钌催化剂在降低水中亚硝胺污染物的应用。
Environ Sci Technol. 2018 Apr 3;52(7):4235-4243. doi: 10.1021/acs.est.7b05834. Epub 2018 Mar 13.
7
[N-nitroso compounds. Analysis and possible carcinogenicity in man].[亚硝基化合物。人体中的分析及潜在致癌性]
IARC Sci Publ (1971). 1976(13):375-85.
8
Occurrence of nine nitrosamines and secondary amines in source water and drinking water: Potential of secondary amines as nitrosamine precursors.水源水和饮用水中 9 种亚硝胺和仲胺的出现:仲胺作为亚硝胺前体的潜力。
Water Res. 2011 Oct 15;45(16):4930-8. doi: 10.1016/j.watres.2011.06.041. Epub 2011 Jul 22.
9
Mutagenicity of N-alkyl-N-(alpha-acetoxyalkyl) nitrosamines in V79 Chinese hamster cells in relation to alkylating activity.N-烷基-N-(α-乙酰氧基烷基)亚硝胺在V79中国仓鼠细胞中的诱变性与烷基化活性的关系
Gan. 1981 Aug;72(4):531-8.
10
Are all nitrosamines concerning? A review of mutagenicity and carcinogenicity data.所有亚硝胺都令人担忧吗?对致突变性和致癌性数据的综述。
Regul Toxicol Pharmacol. 2020 Oct;116:104749. doi: 10.1016/j.yrtph.2020.104749. Epub 2020 Aug 7.

引用本文的文献

1
Carbon quantum dot-based fluorometric detection of nitrosamine impurities in active pharmaceutical ingredients.基于碳量子点的荧光法检测活性药物成分中的亚硝胺杂质
Nanoscale Adv. 2025 Aug 19. doi: 10.1039/d5na00490j.
2
Assessing Nitrosamine Migration from Drinking Water Contact Materials Using a Validated LLE-GC-MS Method.使用经过验证的液液萃取-气相色谱-质谱法评估饮用水接触材料中的亚硝胺迁移情况。
Molecules. 2025 May 30;30(11):2403. doi: 10.3390/molecules30112403.
3
Nitrosamine Drug Substance-Related Impurities (NDSRIs) in Pharmaceuticals: Formation, Mitigation Strategies, and Emphasis on Mutagenicity Risks.

本文引用的文献

1
Rh(III)-Catalyzed Tandem Acylmethylation/Nitroso Migration/Cyclization of Nitrosoanilines with Sulfoxonium Ylides in One Pot: Approach to 3-Nitrosoindoles.铑(III)催化亚硝基苯胺与氧化锍叶立德一锅法串联酰甲基化/亚硝基迁移/环化反应:合成3-亚硝基吲哚的方法
Org Lett. 2020 Jan 17;22(2):361-364. doi: 10.1021/acs.orglett.9b03768. Epub 2020 Jan 2.
2
Synthesis of 2,3-Substituted β--Glycosyl Indoles through C-H Activation/Annulation Process under Rh(III)-Catalysis.通过铑(III)催化的C-H活化/环化过程合成2,3-取代的β-糖基吲哚。
Org Lett. 2020 Jan 3;22(1):57-61. doi: 10.1021/acs.orglett.9b03893. Epub 2019 Dec 20.
3
The surface-enhanced Raman scattering detection of N-nitrosodimethylamine and N-nitrosodiethylamine via gold nanorod arrays with a chemical linkage of zwitterionic copolymer.
药品中的亚硝胺类原料药相关杂质(NDSRIs):形成、缓解策略及对致突变性风险的关注
Pharm Res. 2025 Apr;42(4):547-578. doi: 10.1007/s11095-025-03857-9. Epub 2025 Apr 23.
4
Advancements of paper-based microfluidics and organ-on-a-chip models in cosmetics hazards.基于纸的微流控技术和芯片器官模型在化妆品危害方面的进展。
RSC Adv. 2025 Apr 3;15(13):10319-10335. doi: 10.1039/d4ra07336c. eCollection 2025 Mar 28.
5
Re-Evaluating Acceptable Intake: A Comparative Study of N-Nitrosomorpholine and N-Nitroso Reboxetine Potency.重新评估可接受摄入量:N-亚硝基吗啉与N-亚硝基瑞波西汀效能的比较研究
Environ Mol Mutagen. 2025 Mar;66(3):80-98. doi: 10.1002/em.70007. Epub 2025 Mar 22.
6
Reversible Electrochemical Sensor for NDMA: Leveraging Molecularly Imprinted Polymers for Enhanced Sensitivity and Selectivity.用于N-二甲基亚硝胺的可逆电化学传感器:利用分子印迹聚合物提高灵敏度和选择性。
ACS Sens. 2025 Feb 28;10(2):881-885. doi: 10.1021/acssensors.4c02462. Epub 2025 Jan 30.
7
Optimization of the Cryoprotectants for Direct Vat Set Starters in Sichuan Paocai Using Response Surface Methodology.采用响应面法优化四川泡菜直投式发酵剂的冷冻保护剂
Foods. 2025 Jan 7;14(2):157. doi: 10.3390/foods14020157.
8
Multicomponent reactions (MCRs) yielding medicinally relevant rings: a recent update and chemical space analysis of the scaffolds.生成具有药物相关性环的多组分反应(MCRs):支架的最新进展与化学空间分析
RSC Adv. 2025 Jan 16;15(2):1447-1489. doi: 10.1039/d4ra06681b. eCollection 2025 Jan 9.
9
Reactivities of -Nitrosamines against Common Reagents and Reaction Conditions.亚硝胺对常见试剂及反应条件的反应活性
Org Process Res Dev. 2024 Sep 18;28(10):3837-3846. doi: 10.1021/acs.oprd.4c00217. eCollection 2024 Oct 18.
10
Sensitive determination of volatile nitrosamines with ambient pressure ammonium-adduct ionization mass spectrometry.常压铵加成电离质谱法灵敏测定挥发性亚硝胺。
Anal Bioanal Chem. 2024 Dec;416(29):6839-6847. doi: 10.1007/s00216-024-05580-7. Epub 2024 Oct 14.
通过带有两性离子共聚物化学连接的金纳米棒阵列对 N-亚硝基二甲胺和 N-亚硝基二乙胺的表面增强拉曼散射检测。
Nanoscale. 2020 Jan 14;12(2):1075-1082. doi: 10.1039/c9nr09404k. Epub 2019 Dec 17.
4
Surface-enhanced Raman scattering-based detection of hazardous chemicals in various phases and matrices with plasmonic nanostructures.基于等离子体纳米结构的表面增强拉曼散射在不同相和基质中对危险化学品的检测。
Nanoscale. 2019 Nov 21;11(43):20379-20391. doi: 10.1039/c9nr07439b. Epub 2019 Oct 23.
5
Chemiresistive Carbon Nanotube Sensors for -Nitrosodialkylamines.用于亚硝酰二烷基胺的化学电阻式碳纳米管传感器。
ACS Sens. 2019 Oct 25;4(10):2819-2824. doi: 10.1021/acssensors.9b01532. Epub 2019 Oct 1.
6
Field demonstration of N-Nitrosodimethylamine (NDMA) treatment in groundwater using propane biosparging.采用丙烷生物气提技术对地下水进行 N-亚硝基二甲胺(NDMA)处理的现场示范
Water Res. 2019 Nov 1;164:114923. doi: 10.1016/j.watres.2019.114923. Epub 2019 Jul 28.
7
Water-Mediated Reduction of Aqueous N-Nitrosodimethylamine with Pd.水促进的 Pd 还原水溶液中的 N-亚硝基二甲胺
Environ Sci Technol. 2019 Jul 2;53(13):7551-7563. doi: 10.1021/acs.est.9b01425. Epub 2019 Jun 24.
8
Formation of N-nitrosamines during the analysis of municipal secondary biological nutrient removal process effluents by US EPA method 521.在使用美国环保署方法 521 分析城市二级生物营养去除工艺废水时形成的亚硝胺。
Chemosphere. 2019 Apr;221:597-605. doi: 10.1016/j.chemosphere.2019.01.053. Epub 2019 Jan 9.
9
Lower molecular weight fractions of PolyDADMAC coagulants disproportionately contribute to N-nitrosodimethylamine formation during water treatment.聚二甲基二烯丙基氯化铵(PolyDADMAC)混凝剂的低分子量级分在水处理过程中不成比例地促成了亚硝二甲胺(N-nitrosodimethylamine)的形成。
Water Res. 2019 Mar 1;150:466-472. doi: 10.1016/j.watres.2018.12.002. Epub 2018 Dec 5.
10
Simultaneous Adsorption and Electrochemical Reduction of N-Nitrosodimethylamine Using Carbon-TiO Composite Reactive Electrochemical Membranes.采用碳-二氧化钛复合反应电化学膜同步吸附和电化学还原 N-亚硝基二甲胺。
Environ Sci Technol. 2019 Jan 15;53(2):928-937. doi: 10.1021/acs.est.8b05933. Epub 2018 Dec 28.