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HomeProduct name listSPIPERONE

SPIPERONE

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

  • CAS NO.:749-02-0
  • Empirical Formula: C23H26FN3O2
  • Molecular Weight: 395.47
  • MDL number: MFCD00055099
  • EINECS: 212-024-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 11:59:05
SPIPERONE Structural

What is SPIPERONE?

Chemical properties

Off-White Solid

Originator

Spiropitan,Eisai,Japan,1969

The Uses of SPIPERONE

Spiperone is an antipsychotic.

The Uses of SPIPERONE

antibacterial

What are the applications of Application

Spiperone-d5 is a deuterium-labeled analogue of Spiperone

Definition

ChEBI: 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 Process

A 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 name

Spiropitan (Janssen Pharmaceutica, Belgium).

Therapeutic Function

Tranquilizer

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.

Biological Activity

5-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 Actions

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

Properties of SPIPERONE

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
pka pKa 8.31 (Uncertain);9.09 (Uncertain)
color  light yellow
Water Solubility  32mg/L(22 ºC)

Safety information for SPIPERONE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H361:Reproductive toxicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for SPIPERONE

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