Cirazoline

Cirazoline is a full agonist at the α1A adrenergic receptor, a partial agonist at both the α1B and α1D adrenergic receptors,[1] and a nonselective antagonist to the α2 adrenergic receptor.[2] It is believed that this combination of properties could make cirazoline an effective vasoconstricting agent.[2]

Cirazoline
Names
Preferred IUPAC name
2-[(2-Cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Cirazoline
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) Y
    Key: YAORIDZYZDUZCM-UHFFFAOYSA-N Y
  • 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 mass 216.279 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Cirazoline has also been shown to decrease food intake in rats, purportedly through activation of α1 adrenoceptors in the paraventricular nucleus in the hypothalamus 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] However in preliminary studies, through stimulation of α2 adrenoceptors, working memory is comparatively improved.[4]

References
  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. Ruffolo, 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. 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. Arnsten, 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.


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