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SML0272

Sigma-Aldrich

Etifoxine hydrochloride

≥98% (HPLC)

Synonym(s):

6-Chloro-2-(ethylamino)-4-methyl-4-phenyl-4H-3,1-benzoxazine hydrochloride, 6-Chloro-2-N-ethyl-4-methyl-4-phenyl-4H-3,1-benzoxazin-2-amine hydrochloride, HOE-36801 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H17ClN2O · HCl
CAS Number:
56776-32-0
Molecular Weight:
337.24
EC Number:
260-380-0
MDL number:
MFCD18086857
UNSPSC Code:
12352200
PubChem Substance ID:
329825280
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: ≥5 mg/mL

storage temp.

−20°C

SMILES string

Cl.CCNC1=Nc2ccc(Cl)cc2C(C)(O1)c3ccccc3

InChI

1S/C17H17ClN2O.ClH/c1-3-19-16-20-15-10-9-13(18)11-14(15)17(2,21-16)12-7-5-4-6-8-12;/h4-11H,3H2,1-2H3,(H,19,20);1H

InChI key

SCBJXEBIMVRTJE-UHFFFAOYSA-N

Application

Etifoxine hydrochloride has been used as a γ-aminobutyric acid (GABA)-receptor agonist to study its effects on insulin expression in α cell line (αTC1)

Biochem/physiol Actions

Etifoxine is an anxiolytic anticonvulsant, which promotes axonal regeneration. It binds to β2 and β3 subunits of the GABAA receptor complex, a different target site to benzodiazepines, and binds to the translocator protein (18 kDa) TSPO, formerly known as the peripheral or mitochondrial benzodiazepine receptor. TSPO carries cholesterol from the outer to the inner mitochondrial membrane, which is the rate-limiting step of steroidogenesis. Whereas, its anxiolytic effects involve GABAA receptors and TSPO, etifoxine′s neuroregenerative effects mainly involve TSPO.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Artemisinins target GABAA receptor signaling and impair alpha cell identity
Li J, et al.
Cell, 168(1-2), 86-100 (2017)
Hui Zhang et al.
Brain research bulletin, 165, 178-184 (2020-10-20)
The translocator protein (TSPO), once known as peripheral-type benzodiazepine receptor, was reported to be related with several physiological functions. Etifoxine is a clinically available anxiolytic drug, and has recently shown neuroprotective effects as a TSPO ligand. The aim of the
Jin Li et al.
Cell, 168(1-2), 86-100 (2016-12-06)
Type 1 diabetes is characterized by the destruction of pancreatic β cells, and generating new insulin-producing cells from other cell types is a major aim of regenerative medicine. One promising approach is transdifferentiation of developmentally related pancreatic cell types, including glucagon-producing

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