749-02-0 Usage
Chemical Properties
Off-White Solid
Originator
Spiropitan,Eisai,Japan,1969
Uses
Different sources of media describe the Uses of 749-02-0 differently. You can refer to the following data:
1. Spiperone is an antipsychotic.
2. Antipsychotic
3. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 749-02-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,4 and 9 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 749-02:
(5*7)+(4*4)+(3*9)+(2*0)+(1*2)=80
80 % 10 = 0
So 749-02-0 is a valid CAS Registry Number.
InChI:InChI=1/C23H26FN3O2.ClH/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);1H
749-02-0Relevant articles and documents
Design of a True Bivalent Ligand with Picomolar Binding Affinity for a G Protein-Coupled Receptor Homodimer
Pulido, Daniel,Casadó-Anguera, Verònica,Pérez-Benito, Laura,Moreno, Estefanía,Cordomí, Arnau,López, Laura,Cortés, Antoni,Ferré, Sergi,Pardo, Leonardo,Casadó, Vicent,Royo, Miriam
supporting information, p. 9335 - 9346 (2018/10/24)
Bivalent ligands have emerged as chemical tools to study G protein-coupled receptor dimers. Using a combination of computational, chemical, and biochemical tools, here we describe the design of bivalent ligand 13 with high affinity (KDB1 = 21 pM) for the dopamine D2 receptor (D2R) homodimer. Bivalent ligand 13 enhances the binding affinity relative to monovalent compound 15 by 37-fold, indicating simultaneous binding at both protomers. Using synthetic peptides with amino acid sequences of transmembrane (TM) domains of D2R, we provide evidence that TM6 forms the interface of the homodimer. Notably, the disturber peptide TAT-TM6 decreased the binding of bivalent ligand 13 by 52-fold and had no effect on monovalent compound 15, confirming the D2R homodimer through TM6 ex vivo. In conclusion, by using a versatile multivalent chemical platform, we have developed a precise strategy to generate a true bivalent ligand that simultaneously targets both orthosteric sites of the D2R homodimer.
Practical synthesis of p-aminophenethylspiperone (NAPS), a high-affinity, selective D2-dopamine receptor antagonist
Jin, Chunyang,Mayer, Louise D.,Lewin, Anita H.,Rehder, Kenneth S.,Brine, George A.
, p. 816 - 823 (2008/09/16)
Because attempts to scale up the published synthetic preparation of p-aminophenethylspiperone (NAPS) by N-alkylation of spiperone with 4-nitrophenethyl bromide followed by reduction gave poor yields and difficulties during purification, an alternative synthetic approach has been developed. Use of 4-(N-tert-butyloxycarbonyl) aminophenethyl bromide to alkylate spiperone followed by the Boc group deprotection gave NAPS in 56% yield. This procedure provides an improved and efficient synthesis of the important high-affinity, selective D2-dopamine receptor antagonist NAPS. Copyright Taylor & Francis Group, LLC.
