Imidazoline

Imidazoline
IUPAC name

4,5-Dihydro-1H-imidazole
Identifiers
CAS number 504-75-6 Y
PubChem 68156
ChemSpider 61464 Y
ChEBI CHEBI:53094 Y
Jmol-3D images Image 1
Properties
Molecular formula C3H6N2
Molar mass 70.09 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Imidazoline is a nitrogen-containing heterocycle with formula C3H6N2, 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.


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 generic names include oxymetazoline, xylometazoline, tetrahydrozoline, and naphazoline.

See also

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. PMC 1575965. PMID 15545290. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1575965.