Cirazoline

Cirazoline
Names
	Preferred IUPAC name 2-[(2-Cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole
Identifiers
CAS Number	59939-16-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL13852 ;
ChemSpider	2663 ;
IUPHAR/BPS	515;
MeSH	Cirazoline
PubChem CID	2765;
UNII	QK318GVY3Y ;
CompTox Dashboard (EPA)	DTXSID4045131 ;
	InChI 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) Key: YAORIDZYZDUZCM-UHFFFAOYSA-N ; 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;
	SMILES O(c1c(cccc1)C2CC2)CC/3=N/CCN\3;
Properties
Chemical formula	C13H16N2O
Molar mass	216.284 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cirazoline is a full agonist at the α_1A adrenergic receptor, a partial agonist at both the α_1B and α_1D 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 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]^[5] However, in preliminary studies, through stimulation of α₂ adrenoceptors, working memory is comparatively improved.^[4]

References

^ 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.
^ ^a ^b 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.
^ 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.
^ ^a ^b 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. PMID 9264070. S2CID 20663570.
^ 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)

[horie-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.

[ruffolo-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.

[davies-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.

[:0-4] 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. 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)

[1]

[2]

[3]

[4]

[5]