| Identification | Back Directory | [Name]
CIRAZOLINE HYDROCHLORIDE | [CAS]
40600-13-3 | [Synonyms]
LD-3098
Cirazoline hydrochlo
LD 3098 hydrochloride
CIRAZOLINE HYDROCHLORIDE
CIRAZOLINE HYDROCHLORIDE SELECTIVE A1 AD RENOCE
2-(2-CYCLOPROPYLPHENOXYMETHYL)IMIDAZOLINE HYDROCHLORIDE
2-[(2-cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazolium chloride
2-[(2-CYCLOPROPYLPHENOXY)METHYL]-4,5-DIHYDRO-1H-IMIDAZOLE HYDROCHLORIDE | [EINECS(EC#)]
254-995-3 | [Molecular Formula]
C13H17ClN2O | [MDL Number]
MFCD00274034 | [MOL File]
40600-13-3.mol | [Molecular Weight]
252.74 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at RT | [solubility ]
H2O: >35 mg/mL | [form ]
solid | [color ]
white | [Water Solubility ]
H2O: >35mg/mL | [InChI]
1S/C13H16N2O.ClH/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);1H | [InChIKey]
XFRXWLWUUDJHPB-UHFFFAOYSA-N | [SMILES]
Cl[H].C1CN=C(COc2ccccc2C3CC3)N1 |
| Hazard Information | Back Directory | [Description]
Cirazoline is an α1-adrenergic receptor (α1-AR) agonist (Kis = 120, 960, and 660 nM for recombinant α1A-, α1B-, and α1D-ARs, respectively, in CHO cell membranes). It acts as a full agonist at α1A- and a partial agonist at α1B- and α1D-ARs in vitro (EC50s = 70.7, 79.4, and 239.8 nM, respectively). It also acts as an antagonist at α2-ARs with a pA2 value of 7.56 to inhibit the norepinephrine-induced twitch response in isolated pig ileum. Cirazoline (0.01-1 μg/kg) decreases blood pressure when administered via microinjection to the nucleus reticularis lateralis (NRL) of anesthetized normotensive cats. It enhances spatial memory and reduces depressive- and anxiety-like behavior in mice when administered at a concentration of 10 mg/L in drinking water for 2-9 months. It also enhances performance in the variable delayed response task in aged rhesus monkeys at high doses of 1-10 μg/kg but impairs performance at lower doses of 0.01-1 μg/kg. | [Uses]
Cirazoline hydrochloride has been used to activate the α1-noradrenergic receptors and to study the inhibitory effect of neurokinin1 (NK1) antagonists on respiratory activity using the brainstem transverse slice. | [Biological Activity]
Selective α 1 agonist. Also available as part of the α 1 -Adrenoceptor Tocriset™ and Mixed Adrenergic Tocriset™ . | [Biochem/physiol Actions]
Cirazoline is a selective α1-adrenoceptor agonist and also a non-selective ligand for the imidazoline binding site. Cirazoline dereases spatial working memory performance in aged monkeys. | [storage]
Store at RT | [References]
[1] KUNIKO HONE. Selectivity of the imidazoline α-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned α1-adrenoceptor subtypes[J]. British Journal of Pharmacology, 1995, 116 1: 1611-1618. DOI: 10.1111/j.1476-5381.1995.tb16381.x
[2] ROBERT R. RUFFOLO JR. JAMES E W. RECEPTOR INTERACTIONS OF IMIDAZOLINES: α-ADRENOCEPTORS OF RAT AND RABBIT AORTAE DIFFERENTIATED BY RELATIVE POTENCIES, AFFINITIES AND EFFICACIES OF IMIDAZOLINE AGONISTS[J]. British Journal of Pharmacology, 1982, 77 1: 169-176. DOI: 10.1111/j.1476-5381.1982.tb09283.x
[3] P BOUSQUET J S J Feldman. Central cardiovascular effects of alpha adrenergic drugs: differences between catecholamines and imidazolines.[J]. Journal of Pharmacology and Experimental Therapeutics, 1984, 230 1: 232-236.
[4] VAN A DOZE. Long-term α1A-adrenergic receptor stimulation improves synaptic plasticity, cognitive function, mood, and longevity.[J]. Molecular Pharmacology, 2011, 80 4: 747-758. DOI: 10.1124/mol.111.073734
[5] A.F.T. ARNSTEN J. D J. The Alpha-1 Adrenergic Agonist, Cirazoline, Impairs Spatial Working Memory Performance in Aged Monkeys[J]. Pharmacology Biochemistry and Behavior, 1997, 58 1: Pages 55-59. DOI: 10.1016/s0091-3057(96)00477-7 |
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