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E101

S-(−)-Eticlopride hydrochloride

Name: S-(−)-Eticlopride hydrochloride
Brand: SIGMA

≥98% (HPLC), powder

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₁₇H₂₅ClN₂O₃ · HCl

CAS Number:

97612-24-3

Molecular Weight:

377.31

MDL number:

MFCD00055132

PubChem Substance ID:

24278428

Quality Level

100

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

SMILES string

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

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

InChI key

HFJFXXDHVWLIKX-YDALLXLXSA-N

Gene Information

human ... DRD2(1813)

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.

Preparation Note

Solutions may be stored at 4° C for several days

Legal Information

Manufactured and sold with the permission of Astra AB.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Dopaminergic imaging of nonmotor manifestations in a rat model of Parkinson's disease by fMRI

Chen C C V, et al.

Neurobiology of Disease, 49(9), 99-106 (2013)

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)

Bradykinin B2 receptor and dopamine D2 receptor cooperatively contribute to the regulation of neutrophil adhesion to endothelial cells.

Anna Niewiarowska-Sendo et al.

Acta biochimica Polonica, 65(3), 367-375 (2018-08-28)

Leukocyte adhesion to the vascular endothelium contributes to many immunological and inflammatory disorders. These processes have been shown to be mediated by bradykinin receptor type 2 (B2R) and dopamine receptor type 2 (D2R). In a previous study, we reported the

Some in vitro receptor binding properties of [3H]eticlopride, a novel substituted benzamide, selective for dopamine-D2 receptors in the rat brain.

H Hall et al.

European journal of pharmacology, 111(2), 191-199 (1985-05-08)

The substituted benzamide compound eticlopride, (S)-(-)-5-chloro-3-ethyl-N-[(1-ethyl-2-pyrrolidinyl) methyl]-6-methoxysalicylamide hydrochloride (FLB 131), has been shown to selectively block dopamine-D2 binding sites in the rat brain. The compound was tritium-labelled to high specific radioactivity and was used for in vitro receptor binding studies.

Regional in vivo binding of the substituted benzamide [3H]eticlopride in the rat brain: evidence for selective labelling of dopamine receptors.

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

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