Buspirone

Base Information

• Chemical Name: Buspirone
• CAS No.: 36505-84-7
• Molecular Formula: C21H31N5O2
• Molecular Weight: 385.509
• European Community (EC) Number: 253-072-2
• UNII: TK65WKS8HL
• DSSTox Substance ID: DTXSID2022707
• Nikkaji Number: J19.752A
• Wikipedia: Buspirone
• Wikidata: Q412194
• NCI Thesaurus Code: C62013
• RXCUI: 1827
• Pharos Ligand ID: ZMS6ZPFS1KK8
• Metabolomics Workbench ID: 42835
• ChEMBL ID: CHEMBL49
• Mol file: 36505-84-7.mol

Synonyms:Anxut;Apo Buspirone;Apo-Buspirone;Bespar;Busp;Buspar;Buspirone;Buspirone Hydrochloride;Gen Buspirone;Gen-Buspirone;Hydrochloride, Buspirone;Lin Buspirone;Lin-Buspirone;MJ 9022 1;MJ-9022-1;MJ90221;N-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-1-cyclopentanediacetamide;Neurosine;Novo Buspirone;Novo-Buspirone;Nu Buspirone;Nu-Buspirone;PMS Buspirone;PMS-Buspirone;ratio Buspirone;ratio-Buspirone

Chemical Property of Buspirone

Chemical Property:

• Appearance/Colour: white
• Melting Point: 2-8°C
• Refractive Index: 1.7600 (estimate)
• Boiling Point: 613.9 °C at 760 mmHg
• PKA: pKa 7.60±0.01(H2O t=25.0 I=0.1(NaCl)) (Uncertain)
• Flash Point: 325.1 °C
• Density: 1.24g/cm³
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 385.24777525
• Heavy Atom Count: 28
• Complexity: 529

Purity/Quality:

99.9% ^*data from raw suppliers

5-ChloroBuspirone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Sedatives and Hypnotics
• Canonical SMILES: C1CCC2(C1)CC(=O)N(C(=O)C2)CCCCN3CCN(CC3)C4=NC=CC=N4
• Recent ClinicalTrials: Spinal Cord Neuromodulation for Spinal Cord Injury
• Recent EU Clinical Trials: The effect of oral buspirone hydrochloride on esophageal motility, bolus transit and symptoms of dysphagia, in patients with poor esophageal motility: A randomized, double-blind, placebo controlled, cross-over trial with high resolution esophageal manometry and impedance
• Uses: Tranquilizer (minor). Buspirone is an extremely specific drug that could possibly represent a new chemical class of anxiolytics—azaspirones. As an anxiolytic, its activity is equal to that of benzodiazepines; however, it is devoid of anticonvulsant and muscle relaxant properties, which are characteristic of benzodiazepines. 5-Chloro Buspirone is an impurity of Buspirone Hydrochloride (B689850), a non-benzodiazepine anxiolytic and a 5-hydroxytryptamine (5-HT1) receptor agonist.
• Biological Functions: Buspirone (BuSpar) is the first example of a class of anxiolytic agents that can relieve some symptoms of anxiety in doses that do not cause sedation. Buspirone is structurally unrelated to existing psychotropic drugs.
• Clinical Use: Buspirone is effective in general anxiety and in anxiety with depression.

Technology Process of Buspirone

There total 17 articles about Buspirone 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: 97.0%

1,4-dibromo-butane (110-52-1) + N-(2-pyridinyl)piperazine (20980-22-7) + tetramethylene glutarimide (1075-89-4) → BUSPIRONE (36505-84-7)

Guidance literature:

With potassium carbonate; benzyltriethylammonium bromide; Product distribution; 1.) xylene, reflux, 3 h, 2.) reflux, 5 h; other imides and catalysts, variation of reaction time, also in toluene; also 1-(2-quinolinyl)piperazine;

DOI:10.1002/ardp.19923250513

Reference yield: 95.6%

→ BUSPIRONE (36505-84-7)

Guidance literature:

Reference yield: 90.0%

2-chloropyrimidine (1722-12-9,1195939-87-7) + 8-(4-(piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione (80827-59-4) → BUSPIRONE (36505-84-7)

Guidance literature:

With C₄₈H₅₅ClN₂Pd; sodium t-butanolate; In 1,2-dimethoxyethane; at 20 ℃; for 16h; Inert atmosphere; Sealed tube;

upstream raw materials:

1,4-dibromo-butane

N-(2-pyridinyl)piperazine

tetramethylene glutarimide

8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9-dione

Downstream raw materials:

Buspirone N-oxide

6'-Hydroxybuspirone

6,10-dihydroxybuspirone

Refernces

• 1、 -. "Large-steric-hindrance N-heterocyclic carbene palladium complex, preparation method and application thereof, and synthesis method of sonidegib based on large-steric-hindrance N-heterocyclic carbene palladium complex". Paragraph 0195; 0202-0204. . Retrieved 2021/01/24.
• 2、 Labes, Ricardo,Mateos, Carlos,Battilocchio, Claudio,Chen, Yiding,Dingwall, Paul,Cumming, Graham R.,Rincón, Juan A.,Nieves-Remacha, Maria José,Ley, Steven V.. "Fast continuous alcohol amination employing a hydrogen borrowing protocol". supporting information. p. 59 - 63. Retrieved 2019/01/11.