Imidazoline

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]}

Overview

Imidazoline is a nitrogen-containing heterocycle derived from imidazole. The ring contains an imine bond, and the carbons at the 4 and 5 positions are singly bonded, rather than doubly bonded for the case of imidazole. Imidazolines are structurally related to guanidines and amidines.

Chemical relationship of imidazole to its reduced derivatives.

Like imidazole, imidazoline-based compounds have been used as N-heterocyclic carbene ligands on various transition metals. It is found in the commercially available second generation Grubbs’ catalyst.

Biological role

Many imidazolines are biologically active.^[1] Most bio-active derivatives bear a substituent (aryl or alkyl group) on the carbon between the nitrogen centers. Some brand names include oxymetazoline, xylometazoline, tetrahydrozoline, and naphazoline.

References

↑ N. MacInnes and S. Duty (2004). “Locomotor effects of imidazoline I2-site-specific ligands and monoamine oxidase inhibitors in rats with a unilateral 6-hydroxydopamine lesion of the nigrostriatal pathway”. Br J Pharmacol. 143 (8): 952–959. doi:10.1038/sj.bjp.0706019.

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[1] N. MacInnes and S. Duty (2004). “Locomotor effects of imidazoline I2-site-specific ligands and monoamine oxidase inhibitors in rats with a unilateral 6-hydroxydopamine lesion of the nigrostriatal pathway”. Br J Pharmacol. 143 (8): 952–959. doi:10.1038/sj.bjp.0706019.

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