Imidazoline receptor

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Imidazoline
IUPAC name 4,5-dihydro-1H-imidazole
Identifiers
CAS number [504-75-6]
SMILES
Properties
Molecular formula C3H6N2
Molar mass 70.093 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.
Chemical relationship of imidazole to its reduced derivatives.


Second generation Grubbs' catalyst
Second generation Grubbs' catalyst

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.

Receptor

There are several receptors of imidazoline, most notably the I1-imidazoline receptor. The I1-imidazoline receptor results in hydrolysis of phosphatidylcholine. This generates DAG, arachidonic acid and eicosanoids [2]. In addition, the sodium-hydrogen antiporter is inhibited, and enzymes of catecholamine synthesis is induced. The I1-imidazoline receptor may belong to the neurocytokine receptor family, since its signaling pathways are similar to those of interleukins.[2]

Agonists include the antihypertensive moxonidine, while antagonists include idazoxan.

References

  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. 
  2. ^ a b The I1-Imidazoline Receptor and Its Cellular Signaling Pathways PAUL ERNSBERGER, Departments of Nutrition, Medicine, Pharmacology, and Neuroscience, Case Western Reserve School of Medicine, Cleveland, Ohio 44106-4906, USA

Wikipedia content modification information:

  • This page was last modified on 18 June 2008, at 09:19.

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