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Merck
CN

E101

S-(−)-Eticlopride hydrochloride

≥98% (HPLC), D2 dopamine receptor antagonist, powder

Synonym(s):

FLB 131, S-(−)-3-Chloro-5-ethyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-hydroxy-2-methoxybenzamide hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H25ClN2O3 · HCl
CAS Number:
97612-24-3
Molecular Weight:
377.31
UNSPSC Code:
12352200
PubChem Substance ID:
24278428
NACRES:
NA.77
MDL number:
MFCD00055132
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated

Key Documents

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Product Name

S-(−)-Eticlopride hydrochloride, ≥98% (HPLC), powder

SMILES string

Cl.CCN1CCC[C@H]1CNC(=O)c2c(O)c(CC)cc(Cl)c2OC

InChI key

HFJFXXDHVWLIKX-YDALLXLXSA-N

InChI

1S/C17H25ClN2O3.ClH/c1-4-11-9-13(18)16(23-3)14(15(11)21)17(22)19-10-12-7-6-8-20(12)5-2;/h9,12,21H,4-8,10H2,1-3H3,(H,19,22);1H/t12-;/m0./s1

assay

≥98% (HPLC)

form

powder

optical activity

[α]27/D −7.2°, c = 0.3 in methanol(lit.)

storage condition

desiccated

color

off-white

solubility

H2O: soluble >10 mg/mL
ethanol: soluble 2.6 mg/mL
0.1 M HCl: soluble 7 mg/mL

Quality Level

100

Gene Information

human ... DRD2(1813)

Related Categories

Application

S-(−)-Eticlopride hydrochloride has been used in astrocyte-neuron coculture and functional magnetic resonance imaging (fMRI) experiments.

Biochem/physiol Actions

Potent and selective D2 dopamine receptor antagonist. Eticlopride is highly specific for DAD2 receptors than pimozide or haloperidol. The gene encoding the D2 dopamine receptor (DRD2) is linked with a several disorders including Parkinson′s disease, schizophrenia, and susceptibility to alcoholism.

Legal Information

Manufactured and sold with the permission of Astra AB.

Preparation Note

Solutions may be stored at 4° C for several days

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000354623
0000354623
0000104443
0000136150
0000136150

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Saurav Shome et al.
PloS one, 6(9), e25215-e25215 (2011-09-29)
Cutaneous wound healing is a normal physiological process and comprises different phases. Among these phases, angiogenesis or new blood vessel formation in wound tissue plays an important role. Skin is richly supplied by sympathetic nerves and evidences indicate the significant
Structure and linkage of the D2 dopamine receptor and neural cell adhesion molecule genes on human chromosome 11q23
Eubanks J H, et al.
Genomics, 14(4), 1010-1018 (1992)
Ciliary neurotrophic factor mediates dopamine D2 receptor-induced CNS neurogenesis in adult mice
Yang P, et al.
The Journal of Neuroscience, 28(9), 2231-2241 (2008)
C Köhler et al.
European journal of pharmacology, 120(2), 217-226 (1986-01-21)
The novel substituted benzamide eticlopride, (S)-(-)-5-chloro-3-ethyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxy salicylamide hydrochloride (A38503; FLB 131), was radiolabelled to high specific activity and used for in vivo receptor binding studies in the rat brain. Intravenous injections of [3H]eticlopride resulted in a rapid accumulation of radioactivity
The dopamine D2 antagonist eticlopride accelerates extinction and delays reacquisition of food self-administration in rats
Koerber J, et al.
Behavioural Pharmacology, 24(8), 633-633 (2013)
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