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E101

Sigma-Aldrich

S-(−)-Eticlopride hydrochloride

≥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
UNSPSC Code:
12352200
PubChem Substance ID:
24278428
NACRES:
NA.77

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.

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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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)
Melanie Baumgartner et al.
Nature materials, 19(10), 1102-1109 (2020-06-17)
Biodegradable and biocompatible elastic materials for soft robotics, tissue engineering or stretchable electronics with good mechanical properties, tunability, modifiability or healing properties drive technological advance, and yet they are not durable under ambient conditions and do not combine all the
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)
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)
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