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S7395

Sigma-Aldrich

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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250 MG
$163.00

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250 MG
$163.00

About This Item

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

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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.[1] It induces calcium-dependent chloride secretion in the airway and functions as a potential therapeutic target for cystic fibrosis.[2]

Application

Spiperone has been used to block the actions of 5-hydroxytryptamine (5-HT) receptor.[3][4] It also has been used to study its anti tumor effects in glioblastoma (GBM) cell lines.[5]
Spiperone was used to study the role of dopamine receptors in facilitating the male sexual behavior in quails.6

Biochem/physiol Actions

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

Reconstitution

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_germany

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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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
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
Spiperone enhances intracellular calcium level and inhibits the Wnt signaling pathway
Lu D and Carson DA
BioMed Central Pharmacology, 9(1), 13-13 (2009)
D D Fraser et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 11(9), 2812-2820 (1991-09-01)
Interneurons from the CA1 lacunosum-moleculare (L-M) region were isolated by trypsin-hyaluronidase treatment and mechanical trituration of the L-M. Interneurons isolated in this manner were multipolar with several dendritic processes and could be distinguished from CA1 pyramidal neurons. The properties of
Spiperone, identified through compound screening, activates calcium-dependent chloride secretion in the airway
Liang L, et al.
American Journal of Physiology. Cell Physiology, 296(1), C131-C141 (2009)
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