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SPIPERONE

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CAS:749-02-0
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CAS:749-02-0
Purity:99.83% Package:5mg;39USD|10mg;58USD|25mg;92USD

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  • Spiperone
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SPIPERONE Basic information
Product Name:SPIPERONE
Synonyms:1,3,8-triazaspiro(4.5)decan-4-one,8-(4-(4-fluorophenyl)-4-oxobutyl)-1-phenyl;4’-fluoro-4-(4-oxo-1-phenyl-1,3,8-triazaspiro(4,5)decan-8-yl)-butyrophenon;Spiperone-d5;8-(3-p-fluorobenzoyl-1-propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro(4,5)decane;8-triazaspiro(4.5)decan-4-one,8-(3-(p-fluorobenzoyl)propyl)-1-phenyl-3;r5147;8-[3-(P-FLUOROBENZOYL)PROPYL]-1-PHENYL-1,3,8-TRIAZASPIRO[4.5]DECAN-4-ONE;4-PHENYL-8-[3-(4-FLUOROBENZOYL)-PROPYL]-1-OXO-2,4,8-TRIAZASPIRO[4,5]DECANE
CAS:749-02-0
MF:C23H26FN3O2
MW:395.47
EINECS:212-024-0
Product Categories:Serotonin receptor;Amine;Aromatics;Heterocycles;ILOSONE;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:749-02-0.mol
SPIPERONE Structure
SPIPERONE Chemical Properties
Melting point 190-193.60C
Boiling point 630.6±55.0 °C(Predicted)
density 1.1714 (estimate)
storage temp. Store at RT
solubility H2O: slightly soluble0.2mg/mL
form solid
pkapKa 8.31 (Uncertain);9.09 (Uncertain)
color light yellow
Water Solubility 32mg/L(22 ºC)
InChI1S/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)
InChIKeyDKGZKTPJOSAWFA-UHFFFAOYSA-N
SMILESFc1ccc(cc1)C(=O)CCCN2CCC3(CC2)N(CNC3=O)c4ccccc4
Safety Information
Hazard Codes Xn
Risk Statements 22-63
Safety Statements 36/37
WGK Germany 3
RTECS XX8925000
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Repr. 2
MSDS Information
ProviderLanguage
SigmaAldrich English
SPIPERONE Usage And Synthesis
Chemical PropertiesOff-White Solid
OriginatorSpiropitan,Eisai,Japan,1969
UsesSpiperone is an antipsychotic.
Usesantibacterial
DefinitionChEBI: An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.
Manufacturing ProcessA mixture of 4-carbamoyl-4-N-anilinopiperidine and formamide is heated for 12 hours at 170°C. After cooling, the reaction mixture is divided between 100parts water and 900 parts chloroform. The organic layer is separated, dried over MgSO4 filtered and the filtrate is evaporated. The semisolid residue is stirred in ethyl acetate. The undissolved part is filtered off, washed with ethyl acetate, and dried, yielding 1-oxo-4-phenyl-2,4,8- triazaspiro[4.5]decane.
A mixture of 3.2 parts 4-chloro-p-fluoro-butyrophenone, 3.5 parts 1-oxo-4- phenyl-2,4,8-triazaspiro(4,5)decane, 2 parts Na2CO3 and 0.1 part KI in 200 parts hexone is refluxed with stirring for 50 hours. The mixture is cooled to room temperature, 200 parts water are added and the layers are separated. The organic layer is dried over 10 parts MgSO4, filtered and the solvent removed under reduced pressure on the water bath. The residue is treated with 50 parts diisopropylether. The precipitate is filtered on a Buchner filter and recrystallized from 20 parts hexone at room temperature. The solid is filtered off and dried to yield 1-oxo-4-phenyl-8-[3-(4-fluorobenzoyl)-propyl] -2,4,8- triazaspiro(4.5)decane, melting point 190° to 193.6°C, as a light brown amorphous powder.
Brand nameSpiropitan (Janssen Pharmaceutica, Belgium).
Therapeutic FunctionTranquilizer
General DescriptionSpiperone is a butyrophenone antipsychotic agent. It induces calcium-dependent chloride secretion in the airway and functions as a potential therapeutic target for cystic fibrosis.
Biological Activity5-HT 2A serotonin and selective D 2 -like dopamine receptor antagonist (K i values are 0.06, 0.6, 0.08, ~ 350, ~ 3500 nM for D 2 , D 3 , D 4 , D 1 and D 5 receptors respectively). Antipsychotic.
Biochem/physiol ActionsSelective D2 dopamine receptor antagonist; α1B-adrenoceptor antagonist; mixed 5-HT2A/5-HT1 serotonin receptor antagonist; antipsychotic.
SPIPERONE Preparation Products And Raw materials
Raw materialsFormamide-->4-Chloro-4'-fluorobutyrophenone
Preparation ProductsN-(p-Nitrophenethyl)spiperone
Tag:SPIPERONE(749-02-0) Related Product Information
Prazosin Decane 1-PHENYL-1,3,8-TRIAZASPIRO[4.5]DECAN-4-ONE SPIPERONE, [BENZENE RING-3H] (CARBOXYMETHYLOXIMINO)SPIPERONE, HEMIHYDRATE 8-[4-(4-FLUOROPHENYL)-4-OXOBUTYL]-1-PHENYL-1,3,8-TRIAZASPIRO[4,5]DECAN-4-ONE HYDROCHLORIDE Fluspiperone 2'-IODOSPIPERONE, [125I]- 3'-FLUOROBENZYLSPIPERONE MALEATE N-(p-Aminophenethyl)spiperone [3H]SPIPERONE SPIPERONE N-METHYL-8-[4-(4-FLUOROPHENYL)-4-OXOBUTYL]-1-PHENYL-1,3,8-TRIAZASPIRO-[4.5]DECAN-4-ONE HYDROCHLORIDE 3-Bodipy-propanoic Acid N-Phenethylspiperone Amide N-(p-Nitrophenethyl)spiperone N-(P-ISOTHIOCYANATOPHENETHYL)SPIPERONE HYDROCHLORIDE

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