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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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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

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 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.
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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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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I S Geerts et al.
British journal of pharmacology, 127(6), 1327-1336 (1999-08-24)
In humans intimal thickening is aprerequisite of atherosclerosis. Application of a silicone collar around the rabbit carotid artery induces an intimal thickening but in addition it increases the sensitivity to the vasoconstrictor action of serotonin (5-hydroxytryptamine, 5-HT). The 5-HT receptors
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)
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
Sufang Liu et al.
Pain, 160(2), 334-344 (2018-10-17)
Neuropathic pain represents a challenge to clinicians because it is resistant to commonly prescribed analgesics due to its largely unknown mechanisms. Here, we investigated a descending dopaminergic pathway-mediated modulation of trigeminal neuropathic pain. We performed chronic constriction injury of the
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