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Related Concept Videos

2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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.
Cholinergic Receptors: Nicotinic01:15

Cholinergic Receptors: Nicotinic

Nicotinic receptors are ligand-gated ion channels that are activated by acetylcholine and nicotine. Upon activation, they cause a rapid increase in the permeability of cells to K+, Na+, and Ca2+, followed by depolarization and excitation. They are in the autonomic ganglia, skeletal neuromuscular junction, CNS, and adrenal medulla.
There are two types of nicotinic receptors: neuromuscular (NM/NM/N1) and neuronal (NN/NN/N2). The two families differ based on their location and selectivity to...
Physical Properties of Amines01:26

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.
Drugs Acting on Autonomic Ganglia: Stimulants01:23

Drugs Acting on Autonomic Ganglia: Stimulants


Ganglionic stimulants activate NM nicotinic receptors in autonomic ganglia, falling into two categories: nicotine mimetics [e.g., lobeline, dimethylpiperazine, tetramethylammonium] and muscarinic receptor agonists [e.g., muscarine, methacholine]. The first category's action is rapid and blocked by nicotinic receptor antagonists, while the second category's action is delayed and blocked by atropine-like agents. Nicotine, an alkaloid, affects the heart rate by stimulating sympathetic or...
Cholinergic Antagonists: Chemistry and Structure-Activity Relationship01:29

Cholinergic Antagonists: Chemistry and Structure-Activity Relationship

Cholinergic antagonists bind to cholinergic receptors and limit the effects of acetylcholine and other cholinergic agonists. Based on the specific cholinergic receptor affinity, these antagonists are classified as muscarinic or nicotinic. Anticholinergics interrupt parasympathetic innervations while sympathetic innervations remain uninterrupted. Muscarinic antagonists are also called 'muscarinic antagonists', 'antimuscarinics', or 'parasympatholytics'. Nicotinic antagonists are called...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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...

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Related Experiment Video

Updated: Jul 15, 2026

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

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

Published on: September 25, 2017

Nitrosamines as nicotinic receptor ligands.

Hildegard M Schuller1

  • 1Experimental Oncology Laboratory, Department of Pathobiology, College of Veterinary Medicine, University of Tennessee, 2407 River Drive, Knoxville, TN 37996, USA. hmsch@utk.edu

Life Sciences
|April 27, 2007
PubMed
Summary

Nitrosamines like NNK, found in tobacco, activate alpha7 nicotinic acetylcholine receptors (alpha7nAChRs), driving lung cancer cell growth. Green tea and theophylline may prevent this cancer development.

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Area of Science:

  • Oncology
  • Pharmacology
  • Toxicology

Background:

  • Nitrosamines, including NNK and NNN derived from nicotine, are carcinogens formed in the body.
  • These compounds and their metabolites can cause genotoxic effects through DNA adduct formation.
  • The alpha7 nicotinic acetylcholine receptor (alpha7nAChR) is implicated in cellular processes relevant to cancer.

Purpose of the Study:

  • To investigate the interaction of nitrosamines with nicotinic acetylcholine receptors.
  • To elucidate the role of alpha7nAChR in the development of small cell lung cancer (SCLC).
  • To explore potential preventative strategies against NNK-induced lung tumorigenesis.

Main Methods:

  • Assessed binding affinities of NNK, NNN, and DEN to alpha7nAChR and other nAChRs.
  • Examined alpha7nAChR expression and downstream signaling pathways (Ca2+, PKC, Raf-1, ERK1/2, c-myc) in SCLC and pulmonary neuroendocrine cells (PNECs).
  • Utilized a hamster model of pulmonary fibrosis and lung cancer induction, with interventions including green tea and theophylline.

Main Results:

  • NNK demonstrated high affinity for alpha7nAChR, while NNN bound to epibatidine-sensitive nAChRs.
  • Exposure to NNK or nicotine increased alpha7nAChR expression and stimulated proliferation in SCLC/PNECs, particularly under elevated CO2 conditions.
  • NNK, DEN, or nicotine induced SCLC-like tumors in hamsters; green tea and theophylline inhibited NNK-induced tumor development and proliferation.

Conclusions:

  • NNK acts as a potent agonist for alpha7nAChR, driving cell proliferation crucial for SCLC development.
  • The alpha7nAChR/RAF/ERK1/2 pathway is a key target for SCLC development in smokers.
  • Green tea and theophylline show potential as preventative agents against nitrosamine-induced lung cancer.