(S)-(-)-Sulpiride

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Cat.No. 0895 - (S)-(-)-Sulpiride | C15H23N3O4S | CAS No. 23672-07-3
Description: Standard selective D2-like antagonist
Chemical Name: (S)-(-)-5-Aminosulfonyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide
Purity: ≥99% (HPLC)
Datasheet
Citations (21)
Reviews (1)
Literature (5)

Biological Activity for (S)-(-)-Sulpiride

(S)-(-)-Sulpiride is an active enantiomer. Selective D2-like dopamine antagonist (Ki values are ~ 0.015. ~ 0.013, 1, ~ 45 and ~ 77 μM at D2, D3, D4, D1 and D5 receptors respectively).

Racemate also available.

Compound Libraries for (S)-(-)-Sulpiride

(S)-(-)-Sulpiride is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.

Technical Data for (S)-(-)-Sulpiride

M. Wt 341.42
Formula C15H23N3O4S
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 23672-07-3
PubChem ID 688272
InChI Key BGRJTUBHPOOWDU-NSHDSACASA-N
Smiles NS(C1=CC(C(NC[C@]2([H])CCCN2CC)=O)=C(OC)C=C1)(=O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for (S)-(-)-Sulpiride

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 3.41 10 with gentle warming
DMSO 34.14 100

Preparing Stock Solutions for (S)-(-)-Sulpiride

The following data is based on the product molecular weight 341.42. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.93 mL 14.64 mL 29.29 mL
5 mM 0.59 mL 2.93 mL 5.86 mL
10 mM 0.29 mL 1.46 mL 2.93 mL
50 mM 0.06 mL 0.29 mL 0.59 mL

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Product Datasheets for (S)-(-)-Sulpiride

Certificate of Analysis / Product Datasheet
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References for (S)-(-)-Sulpiride

References are publications that support the biological activity of the product.

Seeman and Van Tol (1993) DA D4 receptors bind inactive (+)-aporphines, suggesting neuroleptic role. Sulpiride not stereoselective. Eur.J.Pharmacol. 233 173 PMID: 8097160

Seeman and Van Tol (1994) DA receptor pharmacology. TiPS 15 264 PMID: 7940991

Merck Index 12 9163


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Keywords: (S)-(-)-Sulpiride, (S)-(-)-Sulpiride supplier, selective, D2-like, antagonists, Dopamine, Non-Selective, Receptors, D3, D4, dopaminergic, Non-selective, 0895, Tocris Bioscience

21 Citations for (S)-(-)-Sulpiride

Citations are publications that use Tocris products. Selected citations for (S)-(-)-Sulpiride include:

Yang et al (2004) Inhibition of ATP-sensitive potassium channels by halope. Br J Pharmacol 143 960 PMID: 15533888

Dai et al (2018) Selective blockade of spinal D2DR by levo-corydalmine attenuates MOR tolerance via suppressing PI3K/Akt-MAPK signaling in a MOR-dependent manner. Exp Mol Med 50 148 PMID: 30429454

Dragicevic et al (2014) Cav1.3 channels control D2-autoreceptor responses via NCS-1 in substantia nigra DA neurons. J Neurosci 137 2287 PMID: 24934288

Chuhma et al (2009) DA neuron glutamate cotransmission: frequency-dependent modulation in the mesoventromedial projection. Neuroscience 164 1068 PMID: 19729052

Pedersen et al (2021) A novel luminescence-based-β-arrestin recruitment assay for unmodified receptors. J Biol Chem PMID: 33684444

Beas et al (2018) The locus coeruleus drives disinhibition in the midline thalamus via a dopaminergic mechanism. Nat Neurosci 21 963 PMID: 29915192

Dorst et al (2020) Polysynaptic inhibition between striatal cholinergic interneurons shapes their network activity patterns in a dopamine-dependent manner. Nat Commun 11 5113 PMID: 33037215

Kim et al (2015) Spinal DArgic projections control the transition to pathological pain plasticity via a D1/D5-mediated mechanism. J Neurophysiol 35 6307 PMID: 25904784

Shin et al (2015) Muscarinic regulation of DA and glutamate transmission in the nucleus accumbens. J Clin Invest 112 8124 PMID: 26080439

Marcott et al (2014) Phasic DA release drives rapid activation of striatal D2-receptors. Neuron 84 164 PMID: 25242218

Costa et al (2008) Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition. J Neurosci 28 8040 PMID: 18685029

Maher and Westbrook (2008) Co-transmission of DA and GABA in periglomerular cells. Proc Natl Acad Sci U S A 99 1559 PMID: 18216231

Cilz et al (2014) DArgic modulation of GABAergic transmission in the entorhinal cortex: concerted roles of α1 adrenoreceptors, inward rectifier K+, and T-type Ca2+ channels. Cereb Cortex 24 3195 PMID: 23843440

Kurita et al (2012) HDAC2 regulates atypical antipsychotic responses through the modulation of mGlu2 promoter activity. Nat Neurosci 15 1245 PMID: 22864611

Ishima et al (2012) Neurite outgrowth mediated by the heat shock protein Hsp90α: a novel target for the antipsychotic drug aripipr. Transl Psychiatry 2 e170 PMID: 23047241

Lim et al (2014) A leptin-mediated central mechanism in analgesia-enhanced opioid reward in rats. J Neurosci 34 9779 PMID: 25031415

Wang et al (2006) DArgic control of corticostriatal long-term synaptic depression in medium spiny neurons is mediated by cholinergic interneurons. Neuron 50 443 PMID: 16675398

Brzosko et al (2015) Retroactive modulation of spike timing-dependent plasticity by DA. Elife 4 PMID: 26516682

Jensen (2015) Effects of DA D2-Like Receptor Antagonists on Light Responses of Ganglion Cells in Wild-Type and P23H Rat Retinas. PLoS One 10 e0146154 PMID: 26717015

Ma et al (2015) Agonist and antagonist effects of aripipr. on D2-like receptors controlling rat brain DA synthesis depend on the DArgic tone. Int J Neuropsychopharmacol 18 PMID: 25522390

Baca et al (2013) Gene-environment interactions affect long-term depression (LTD) through changes in DA receptor affinity in Snap25 deficient mice. Brain Res 1532 85 PMID: 23939223


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Reviews for (S)-(-)-Sulpiride

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Selective block of dopamine receptors.
By Sergiy Sylantyev on 10/15/2020
Species: Human
Cell Line/Tissue: Stem cell - derived neurons

(S)‐sulpiride (Sul) was in use to block D2 dopamine receptors and thus prevent D2-mediated suppression of NMDA receptors response. The compound worked as expected, generating a discernible increase of amplitudes of NMDA-receptor – mediated evoked post-synaptic potentials in cultured dopamine neurons when applied with SCH‐23390 (see illustration). No problem with dissolution in DMSO for 10 mM stock.

Reference
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