Gepirone

Base Information

• Chemical Name: Gepirone
• CAS No.: 83928-76-1
• Molecular Formula: C19H29 N5 O2
• Molecular Weight: 359.472
• Hs Code.: 2933990090
• UNII: JW5Y7B8Z18
• DSSTox Substance ID: DTXSID90232813
• Nikkaji Number: J40.720H
• Wikipedia: Gepirone
• Wikidata: Q2650256
• NCI Thesaurus Code: C74193
• Pharos Ligand ID: 7PV68P3A4YW2
• Metabolomics Workbench ID: 144625
• ChEMBL ID: CHEMBL284092
• Mol file: 83928-76-1.mol

Synonyms:4,4-dimethyl-1-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-2,6-piperidinedione;BMY 13805;BMY-13805;gepirone;gepirone monohydrochloride;MJ 13805;MJ 13805-1;MJ-13805

Chemical Property of Gepirone

Chemical Property:

• Boiling Point: 562.3±60.0 °C(Predicted)
• PKA: 7.72±0.10(Predicted)
• PSA: 69.64000
• Density: 1.142±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 1.49480
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 359.23212518
• Heavy Atom Count: 26
• Complexity: 476

Purity/Quality:

99% ^*data from raw suppliers

Gepirone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC(=O)N(C(=O)C1)CCCCN2CCN(CC2)C3=NC=CC=N3)C
• Recent ClinicalTrials: Gepirone vs Placebo in Treatment of Cocaine Dependence - 3
• Description: Gepirone is a chemical analogue of buspirone and also acts as a partial agonist at 5-HT1A receptors. It is active in animal models predictive of anxiolytic action and also shows antidepressant activity in preclinical studies. With long-term administration, gepirone downregulates 5-HT2 receptors, which is a property common to nearly all antidepressant drugs (Stahl 1994). This dual action, suggesting both anxiolytic and antidepressant effects, is typical of many compounds acting at 5-HT1A receptors and may indicate that such compounds may be useful in the treatment of mixed anxiety and depression (Stahl, in press). Preliminary phase II clinical data have shown that gepirone is an effective anxiolytic that significantly reduces both psychic and somatic symptoms of generalized anxiety disorder. Like buspirone, gepirone does not impair memory, verbal fluency, or psychomotor performance (Harto and Branconnier 1988).
• Uses: Gepirone is an antidepressant and anxiolytic of the azapirone class. It acts as a selective partial agonist of the 5-HT1A receptor.

Technology Process of Gepirone

There total 14 articles about Gepirone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

4-(pyrimidin-2-yl)piperazin-1-yl benzoate + (4-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)butyl)zinc chloride → gepirone (83928-76-1)

Guidance literature:

With cobalt(II) chloride; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03787

Reference yield: 70.0%

4,4-dimethyl-1-<4-(4-pyrimidin-2-yl-piperazin-1-yl)but-2-en-1-yl>piperidine-2,6-dione (124475-86-1) → gepirone (83928-76-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; under 760 Torr;

Reference yield:

2,2-dimethylglutarimide (1194-33-8) + 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane hydroxide → gepirone (83928-76-1)

Guidance literature:

In toluene;

upstream raw materials:

1,4-dibromo-butane

3,3-dimethyl glutarimide

N-(2-pyridinyl)piperazine

8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane Bromide

Refernces

• 1、 Tandon, Manish,O'Donnell, Mary-Margaret,Porte, Alex,Vensel, David,Yang, Donglai,Palma, Rocio,Beresford, Alan,Ashwell, Mark A.. "The design and preparation of metabolically protected new arylpiperazine 5-HT1A ligands". . p. 1709 - 1712. Retrieved 2007/10/03.
• 2、 Kuo, David L.. "PD(O)-CATALYSED SYHTHESIS OF BUSPIRONE AND GEPIRONE". . p. 1463 - 1470. Retrieved 2007/10/02.