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E3263

Sigma-Aldrich

Efaroxan hydrochloride

≥98% (HPLC)

Synonym(s):

2-Ethyl-2-(imidazolin-2-yl)-2,3-dihydrobenzofuran hydrochloride, RX 821037A

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About This Item

Empirical Formula (Hill Notation):
C13H16N2O · HCl
CAS Number:
89197-00-2
Molecular Weight:
252.74
MDL number:
MFCD00069270
UNSPSC Code:
12352200
PubChem Substance ID:
24278415
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

solubility

H2O: >20 mg/mL

SMILES string

Cl.CCC1(Cc2ccccc2O1)C3=NCCN3

InChI

1S/C13H16N2O.ClH/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13;/h3-6H,2,7-9H2,1H3,(H,14,15);1H

InChI key

DWOIUCRHVWIHAH-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152)

Biochem/physiol Actions

(+)-Isomer is a selective α-adrenoceptor antagonist; (−)-isomer is an imidazoline ligand that induces insulin secretion, mediated by the blockade of ATP-sensitive potassium channels in pancreatic β cells; I1 imidazoline binding site antagonist.

Features and Benefits

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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T L Berridge et al.
European journal of pharmacology, 213(2), 205-212 (1992-03-24)
The effects of efaroxan (RX 821037A; 2-[2-(2-ethyl-2,3-dihydrobenzofuranyl)]-2-imidazoline HCl) at alpha 1- and alpha 2-adrenoceptors were investigated in isolated tissues, pithed rats and conscious rats. In isolated tissues, efaroxan competitively antagonised the inhibitory effects of p-aminoclonidine in the electrically stimulated (0.1
Francesco Gentili et al.
European journal of pharmacology, 553(1-3), 73-81 (2006-11-04)
Some studies, suggesting the involvement of I(2)-imidazoline binding sites (I(2)-IBS) in morphine analgesia modulation, prompted us to examine on mice antinociceptive assays the effect produced by 1 (phenyzoline), that in view of its high I(2)-IBS affinity and high I(2)-IBS selectivity
A Szollosi et al.
British journal of pharmacology, 159(3), 669-677 (2010-02-05)
ATP-sensitive potassium channels (K(ATP) channels) in beta cells are a major target for insulinotropic drugs. Here, we studied the effects of selected stimulatory and inhibitory pharmacological agents in islets lacking K(ATP) channels. We compared insulin secretion (IS) and cytosolic calcium
V Fagerholm et al.
British journal of pharmacology, 154(6), 1287-1296 (2008-05-22)
The imidazoline-type alpha2-adrenoceptor antagonists (+/-)-efaroxan and phentolamine increase insulin secretion and reduce blood glucose levels. It is not known whether they act by antagonizing pancreatic beta-cell alpha2-adrenoceptors or by alpha2-adrenoceptor-independent mechanisms. Many imidazolines inhibit the pancreatic beta-cell KATP channel, which
J C Chapman et al.
Diabetes, 48(12), 2349-2357 (1999-12-02)
The properties of ATP-sensitive K+ (K(ATP)) channels were explored in the electrofusion-derived, glucose-responsive, insulin-secreting cell line BRIN-BD11 using patch-clamp techniques. In intact cells, K(ATP) channels were inhibited by glucose, the sulfonylurea tolbutamide, and the imidazoline compounds efaroxan and phentolamine. Each
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