Cirazoline

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| Watchedfields = changed

| verifiedrevid = 437194318

| ImageFile = Cirazoline.svg

| ImageSize = 180

| PIN = 2-[(2-Cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole

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| Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = QK318GVY3Y

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2663

| 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)

| InChIKey = YAORIDZYZDUZCM-UHFFFAOYAV

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 13852

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = YAORIDZYZDUZCM-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 59939-16-1

| PubChem = 2765

| IUPHAR_ligand = 515

| SMILES = O(c1c(cccc1)C2CC2)CC/3=N/CCN\3

| MeSHName = Cirazoline

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|Section2 = {{Chembox Properties

| C=13 | H=16 | N=2 | O=1

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|Section3 = {{Chembox Hazards

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Cirazoline is a full agonist at the α_1A adrenergic receptor, a partial agonist at both the α_1B and α_1D adrenergic receptors,{{cite journal|author1=Horie, K |author2=Obika, K |author3=Foglar, R. | title = Selectivity of the imidazoline α-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned α₁-adrenoceptor subtypes | journal = British Journal of Pharmacology | year = 1995 | volume = 116 | issue = 1 | pages = 1611–8 | pmid = 8564227 | doi=10.1111/j.1476-5381.1995.tb16381.x | pmc=1908909}} and a nonselective antagonist to the α₂ adrenergic receptor.{{cite journal|author1=Ruffolo, R. R. Jr. |author2=Waddell, J. E. | title = Receptor interactions of imidazolines. IX. Cirazoline is an α₁ adrenergic agonist and an α₂ adrenergic antagonist | journal = Journal of Pharmacology and Experimental Therapeutics | year = 1982 | volume = 222 | issue = 1 | pages = 29–36 |doi=10.1016/S0022-3565(25)33148-4 | pmid = 6123592 }} It is believed that this combination of properties could make cirazoline an effective vasoconstricting agent.

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.{{cite journal |author1=Davies, B. T. |author2=Wellman, P. J. | year = 1992 | title = Effects on ingestive behavior in rats of the α₁-adrenoceptor agonist cirazoline | journal = European Journal of Pharmacology | volume = 210 | issue = 1 | pages = 11–16 | doi = 10.1016/0014-2999(92)90645-K | pmid = 1350985 }} 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.{{Cite journal |last1=Arnsten |first1=A.F.T. |last2=Jentsch |first2=J.D. |date=September 1997 |title=The Alpha-1 Adrenergic Agonist, Cirazoline, Impairs Spatial Working Memory Performance in Aged Monkeys |journal=Pharmacology Biochemistry and Behavior |volume=58 |issue=1 |pages=55–59 |doi=10.1016/s0091-3057(96)00477-7 |pmid=9264070 |s2cid=20663570 |issn=0091-3057|doi-access=free }}{{Cite journal |last=Imbery, Irdmusa, Speidell, Streer, Griffin |first=Ted E., Mitra S., Andrew P., Mark S., John D. |date=15 December 2007 |title=The effects of Cirazoline, an alpha-1 adrenoreceptor agonist, on the firing rates of thermally classified anterior hypothalamic neurons in rat brain slices |journal=Brain Research |volume=1193 |pages=93–101 |doi=10.1016/j.brainres.2007.12.016 |pmid=18184607 |pmc=2268753 }} However, in preliminary studies, through stimulation of α₂ adrenoceptors, working memory is comparatively improved.