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
SMILES N\1=C\NCC/1
InChI InChI=1S/C3H6N2/c1-2-5-3-4-1/h3H,1-2H2,(H,4,5) Y Key: MTNDZQHUAFNZQY-UHFFFAOYSA-N Y InChI=1/C3H6N2/c1-2-5-3-4-1/h3H,1-2H2,(H,4,5) Key: MTNDZQHUAFNZQY-UHFFFAOYAB
Properties
Molecular formula	C3H6N2
Molar mass	70.09 g mol−1
Y (verify) (what is: Y/N?) 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.

Chemical relationship of imidazole to its reduced derivatives.

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

See also

• Imidazoline receptor
• Imidazolidine

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.