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S7395

Spiperone

solid

Synonym(s):

8-[3-(p-Fluorobenzoyl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one, R 5147, Spiroperidol

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About This Item

Empirical Formula (Hill Notation):
C23H26FN3O2
CAS Number:
749-02-0
Molecular Weight:
395.47
NACRES:
NA.77
PubChem Substance ID:
24277908
UNSPSC Code:
12352200
EC Number:
212-024-0
MDL number:
MFCD00055099
Form:
solid
Quality level:
200
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form

solid

Quality Level

200

color

light yellow

solubility

H2O: slightly soluble 0.2 mg/mL, 0.1 M HCl: slightly soluble 0.3 mg/mL, ethanol: 1.5 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2 mg/mL

SMILES string

Fc1ccc(cc1)C(=O)CCCN2CCC3(CC2)N(CNC3=O)c4ccccc4

InChI

1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29)

InChI key

DKGZKTPJOSAWFA-UHFFFAOYSA-N

Gene Information

human ... ADRA1B(147), DRD2(1813), DRD3(1814), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356)
rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413), Adra2a(25083), Drd1a(24316), Drd2(24318), Drd3(29238), Htr1a(24473), Htr2a(29595), Htr2c(25187), Htr7(65032)

General description

Spiperone is a butyrophenone antipsychotic agent. It induces calcium-dependent chloride secretion in the airway and functions as a potential therapeutic target for cystic fibrosis.

Application

Spiperone was used to study the role of dopamine receptors in facilitating the male sexual behavior in quails.6
Spiperone has been used to block the actions of 5-hydroxytryptamine (5-HT) receptor. It also has been used to study its anti tumor effects in glioblastoma (GBM) cell lines.

Biochem/physiol Actions

Selective D2 dopamine receptor antagonist; α1B-adrenoceptor antagonist; mixed 5-HT2A/5-HT1 serotonin receptor antagonist; antipsychotic.

Preparation Note

Solutions may be stored for 1-2 days at 4 °C.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

hcodes

H302,H361

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000231196
0000231196
0000181630
0000173496
0000181630

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Carmen Klein Herenbrink et al.
Nature communications, 7, 10842-10842 (2016-02-26)
Biased agonism describes the ability of ligands to stabilize different conformations of a GPCR linked to distinct functional outcomes and offers the prospect of designing pathway-specific drugs that avoid on-target side effects. This mechanism is usually inferred from pharmacological data
Marion Schuller et al.
ChemMedChem, 12(19), 1585-1594 (2017-08-05)
MS Binding Assays are a label-free alternative to radioligand binding assays. They provide basically the same capabilities as the latter, but use a non-labeled reporter ligand instead of a radioligand. In contrast to radioligand binding assays, MS Binding Assays offer-owing
Spiperone enhances intracellular calcium level and inhibits the Wnt signaling pathway
Lu D and Carson DA
BioMed Central Pharmacology, 9(1), 13-13 (2009)
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