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O2378

Sigma-Aldrich

Oxymetazoline hydrochloride

≥99%, solid

Synonym(s):

2-(3-Hydroxy-2,6-dimethyl-4-t-butylbenzyl)-2-imidazoline hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C16H24N2O · HCl
CAS Number:
2315-02-8
Molecular Weight:
296.84
EC Number:
219-015-0
MDL number:
MFCD00058147
UNSPSC Code:
12352200
PubChem Substance ID:
24277792
NACRES:
NA.77

Quality Level

100

Assay

≥99%

form

solid

solubility

H2O: soluble
alcohol: soluble

originator

Schering Plough

SMILES string

Cl.Cc1cc(c(O)c(C)c1CC2=NCCN2)C(C)(C)C

InChI

1S/C16H24N2O.ClH/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14;/h8,19H,6-7,9H2,1-5H3,(H,17,18);1H

InChI key

BEEDODBODQVSIM-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , HTR1A(3350) , HTR1B(3351) , HTR1D(3352)

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Biochem/physiol Actions

Oxymetazoline hydrochloride is a partial α2A-adrenoceptor agonist; agonist at 5-HT1A, 5-HT1B, and 5-HT1D serotonin receptors. It is a mixed agonist-antagonist at 5-HT1C serotonin receptors.

Features and Benefits

This compound is featured on the α2-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300 + H330,H318,H412

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Aquatic Chronic 3 - Eye Dam. 1

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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P Schoeffter et al.
European journal of pharmacology, 196(2), 213-216 (1991-04-17)
Oxymetazoline was recognized with nanomolar affinity by 5-HT1A, 5-HT1B and 5-HT1D binding sites and mimicked the effects of 5-hydroxytryptamine with about the same potency and intrinsic activity as the endogenous amine in the corresponding functional tests. At 5-HT1C receptors, oxymetazoline
H Law et al.
Journal of medicinal chemistry, 41(13), 2243-2251 (1998-06-19)
Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the
Vittorio Canale et al.
Molecules (Basel, Switzerland), 26(13) (2021-07-03)
The complex pathophysiology of depression, together with the limits of currently available antidepressants, has resulted in the continuous quest for alternative therapeutic strategies. Numerous findings suggest that pharmacological blockade of α2-adrenoceptor might be beneficial for the treatment of depressive symptoms
K Horie et al.
British journal of pharmacology, 116(1), 1611-1618 (1995-09-01)
1. To investigate the structure-activity relationships of alpha-adrenoceptor agonists for the alpha 1-adrenoceptor subtypes, we have compared the imidazoline class of compounds, oxymetazoline and cirazoline, with the phenethylamine, noradrenaline, in their affinities and also in their intrinsic activities in Chinese
Sylwia K Paszun et al.
Acta poloniae pharmaceutica, 70(6), 1079-1085 (2014-01-05)
The presented study aimed at the evaluation of hydrochlorothiazide influence on cilazapril stability in model mixture and fixed dose tablet formulation. The degradation of cilazapril in the presence of hydrochlorothiazide took place according to autocatalytic reaction kinetic mechanism, described mathematically

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