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Toxicity of four nitrogen-heterocyclic polyaromatic hydrocarbons (NPAHs) to soil organisms

K Kobetičová1, J Bezchlebová, J Lána

  • 1RECETOX - Research Centre for Environmental Chemistry and Ecotoxicology, Faculty of Science, Masaryk University, Kamenice 126/3, Brno CZ-62500, Czech Republic.

Ecotoxicology and Environmental Safety
|March 28, 2008
PubMed

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Physical Properties of Amines

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Types of Toxins

Humans continually engage with an environment rich in potentially harmful chemicals. These are introduced to our bodies through inhalation, ingestion, or skin contact. These chemicals exist in various forms, such as air and environmental pollutants, agricultural chemicals, organic solvents, and heavy metals.
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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.
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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).