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Alkylpyrazine alarm pheromones in ponerine ants
Abstract:
The mandibular gland secretions of the ponerine ants Odontomachus hastatus, O. clarus, and O. brunneus contain alkylpyrazines. These compounds, 2,5-dimethyl-3-isopentylpyrazine in O. hastatus and O. clarus, and 2,6-dimethyl-3-pentyl-, -butyl-, -propyl-, and -ethyl-pyrazines in O. brunneus, have previously not been found as animal natural products. These compounds function as powerful releasers of alarm behavior for Odontomachus workers and are probably also utilized as defensive compounds.
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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.
Basicity of Heterocyclic Aromatic Amines
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).

