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

pka

pKa 8.31 (Uncertain);9.09 (Uncertain)

form 

solid

color 

light yellow

Water Solubility 

32mg/L(22 ºC)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-63

Safety Statements 

36/37

WGK Germany 

3

RTECS 

XX8925000

MSDS

• Language:English Provider:SigmaAldrich

SPIPERONE Usage And Synthesis

Chemical Properties

Off-White Solid

Originator

Spiropitan,Eisai,Japan,1969

Uses

Spiperone is an antipsychotic.

Uses

antibacterial

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.

SPIPERONE(749-02-0)Related Product Information

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