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Cirazoline

From Wikipedia, the free encyclopedia
Cirazoline
Names
Preferred IUPAC name
2-[(2-Cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSHCirazoline
UNII
  • InChI=1S/C13H16N2O/c1-2-4-12(11(3-1)10-5-6-10)16-9-13-14-7-8-15-13/h1-4,10H,5-9H2,(H,14,15) checkY
    Key: YAORIDZYZDUZCM-UHFFFAOYSA-N checkY
  • InChI=1/C13H16N2O/c1-2-4-12(11(3-1)10-5-6-10)16-9-13-14-7-8-15-13/h1-4,10H,5-9H2,(H,14,15)
    Key: YAORIDZYZDUZCM-UHFFFAOYAV
  • O(c1c(cccc1)C2CC2)CC/3=N/CCN\3
Properties
C13H16N2O
Molar mass216.284 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Cirazoline is a fullagonist at theα1A adrenergic receptor, apartial agonist at both theα1B andα1D adrenergic receptors,[1] and a nonselectiveantagonist to theα2 adrenergic receptor.[2] It is believed that this combination of properties could make cirazoline an effectivevasoconstricting agent.[2]

Cirazoline has also been shown to decrease food intake in rats, purportedly through activation of α1 adrenoceptors in theparaventricular nucleus in thehypothalamus of the brain.[3] Administration of cirazoline also seemed to present impairment in the spatial memory of monkeys through the activation of the same receptors that showed decreased food intake in rats.[4][5] However, in preliminary studies, through stimulation of α2 adrenoceptors, working memory is comparatively improved.[4]

References

[edit]
  1. ^Horie, K; Obika, K; Foglar, R. (1995)."Selectivity of the imidazoline α-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned α1-adrenoceptor subtypes".British Journal of Pharmacology.116 (1):1611–8.doi:10.1111/j.1476-5381.1995.tb16381.x.PMC 1908909.PMID 8564227.
  2. ^abRuffolo, R. R. Jr.; Waddell, J. E. (1982). "Receptor interactions of imidazolines. IX. Cirazoline is an α1 adrenergic agonist and an α2 adrenergic antagonist".Journal of Pharmacology and Experimental Therapeutics.222 (1):29–36.doi:10.1016/S0022-3565(25)33148-4.PMID 6123592.
  3. ^Davies, B. T.; Wellman, P. J. (1992). "Effects on ingestive behavior in rats of the α1-adrenoceptor agonist cirazoline".European Journal of Pharmacology.210 (1):11–16.doi:10.1016/0014-2999(92)90645-K.PMID 1350985.
  4. ^abArnsten, A.F.T.; Jentsch, J.D. (September 1997)."The Alpha-1 Adrenergic Agonist, Cirazoline, Impairs Spatial Working Memory Performance in Aged Monkeys".Pharmacology Biochemistry and Behavior.58 (1):55–59.doi:10.1016/s0091-3057(96)00477-7.ISSN 0091-3057.PMID 9264070.S2CID 20663570.
  5. ^Imbery, Irdmusa, Speidell, Streer, Griffin, Ted E., Mitra S., Andrew P., Mark S., John D. (15 December 2007)."The effects of Cirazoline, an alpha-1 adrenoreceptor agonist, on the firing rates of thermally classified anterior hypothalamic neurons in rat brain slices".Brain Research.1193:93–101.doi:10.1016/j.brainres.2007.12.016.PMC 2268753.PMID 18184607.{{cite journal}}: CS1 maint: multiple names: authors list (link)
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
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