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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;Intermediates & Fine Chemicals;Aromatics;Heterocycles;ILOSONE;Pharmaceuticals | | Mol File: | 749-02-0.mol |
| 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) |
| Hazard Codes | Xn | | Risk Statements | 22-63 | | Safety Statements | 36/37 | | WGK Germany | 3 | | RTECS | XX8925000 |
| SPIPERONE Usage And Synthesis |
| Chemical Properties | Off-White Solid | | Originator | Spiropitan,Eisai,Japan,1969 | | Uses | Spiperone is an antipsychotic. | | Uses | 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 Preparation Products And Raw materials |
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