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Updated: May 30, 2026

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

Occurrence of nine nitrosamines and secondary amines in source water and drinking water: Potential of secondary

Wanfeng Wang¹, Shuoyi Ren, Haifeng Zhang

¹State Key Laboratory of Environmental Aquatic Chemistry, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.

|August 17, 2011

Abstract:

Due to their high carcinogenicity, the control of nitrosamines, a group of disinfection by-products (DBPs), is an important issue for drinking water supplies. In this study, a method using ultra-performance liquid chromatography-electrospray ionization tandem mass spectrometry was improved for simultaneously analyzing nine nitrosamines in source water and finished water samples of twelve drinking water treatment plants (DWTPs) in China. The method detection limits of the nine target analytes were 0.2-0.9 ng/L for the source water samples and 0.1-0.7 ng/L for the finished water samples. Of the nine nitrosamines, six (N-nitrosodimethylamine (NDMA), nitrosodiethylamine (NDEA), N-nitrosomorpholine (NMor), N-nitrosodi-n-butylamine (NDBA), N-nitrosomethylethylamine (NMEA), and N-nitrosodiphenylamine (NDPhA)) were detected. The total nitrosamine concentrations in source water and finished water samples were no detection-42.4 ng/L and no detection-26.3 ng/L, respectively, and NDMA (no detection-13.9 ng/L and no detection-20.5 ng/L, respectively) and NDEA (no detection-16.3 ng/L and no detection-14.0 ng/L, respectively) were the most abundant. Meanwhile, the occurrence of nine secondary amines corresponding to the nine nitrosamines was also investigated. All of them except for di-n-propylamine were detected in some source water and finished water samples, and dimethylamine (no detection-3.9 μg/L and no detection-4.0 μg/L, respectively) and diethylamine (no detection-2.4 μg/L and no detection-1.8 μg/L, respectively) were the most abundant ones. Controlled experiments involving chloramination of four secondary amines confirmed that dimethylamine, diethylamine, morpholine and di-n-butylamine in water can form the corresponding nitrosamines, with diethylamine and morpholine showing significantly higher yields than dimethylamine which has already been identified as a precursor of NDMA. This study proved that diethylamine, morpholine and di-n-butylamine detected in raw water would be one of the important the precursors of NDEA, NMOR and NDBA, respectively, in drinking water.

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2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

Physical Properties of Amines

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.

Amines: Introduction

Amines: Introduction

Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

Nomenclature of Secondary and Tertiary Amines

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

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