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C223

Sigma-Aldrich

Cirazoline hydrochloride

solid

Synonym(s):

2-[(2-Cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C13H16N2O · HCl
CAS Number:
40600-13-3
Molecular Weight:
252.74
EC Number:
254-995-3
MDL number:
MFCD00274034
UNSPSC Code:
12352200
PubChem Substance ID:
24277770
NACRES:
NA.77

form

solid

Quality Level

100

color

white

solubility

H2O: >35 mg/mL

SMILES string

Cl[H].C1CN=C(COc2ccccc2C3CC3)N1

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

InChI key

XFRXWLWUUDJHPB-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146)

Application

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.

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.

Features and Benefits

This compound is featured on the α1-Adrenoceptors and Imidazoline Binding Sites pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Bronwyn A Evans et al.
Molecular pharmacology, 79(2), 298-307 (2010-10-28)
Although G protein-coupled receptors are often categorized in terms of their primary coupling to a given type of Gα protein subunit, it is now well established that many show promiscuous coupling and activate multiple signaling pathways. Furthermore, some agonists selectively
Aarthi Kamath et al.
The international journal of neuropsychopharmacology, 11(8), 1085-1096 (2008-05-08)
Neonatal ventral hippocampus (nVH) lesion in rats is a widely used animal model of schizophrenia due to the predominantly post-pubertal emergence of many schizophrenia-like behaviours. Our previous studies have shown increased ligand binding of alpha1 adrenergic receptors (AR) in the
Jinhwan Kim et al.
Molecules (Basel, Switzerland), 24(4) (2019-02-24)
Although melanin production is a key self-defense mechanism against ultraviolet radiation (UVR)-induced skin damage, uneven or excessive deposition of melanin causes hyperpigmentary disorders. Currently available whitening agents are unsatisfactory because of issues with efficacy and safety. To develop more effective
Karen M Alsene et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 31(10), 2150-2161 (2006-01-13)
Prepulse inhibition (PPI) refers to the attenuation of startle when a weak prestimulus precedes the startling stimulus. PPI is deficient in several psychiatric illnesses involving poor sensorimotor gating. Previous studies indicate that alpha1 adrenergic receptors regulate PPI, yet the extent
Vito Bellantuono et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 148(2), 160-164 (2008-06-12)
Frog skin transports ions and water under hormonal control. In spite of the fundamental role played by adrenergic stimulation in maintaining the water balance of the organism, the receptor subtype(s) present in the skin have not been identified yet. We
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