Volinanserin

Base Information

• Chemical Name: Volinanserin
• CAS No.: 139290-65-6
• Molecular Formula: C22H28 F N O3
• Molecular Weight: 373.468
• Hs Code.: 2933399090
• UNII: EW71EE171J
• DSSTox Substance ID: DTXSID6047363
• Nikkaji Number: J555.944H
• Wikipedia: Volinanserin
• Wikidata: Q7940202
• NCI Thesaurus Code: C95220
• Pharos Ligand ID: 2K25XQD57JGB
• Metabolomics Workbench ID: 144363
• ChEMBL ID: CHEMBL74355
• Mol file: 139290-65-6.mol

Synonyms:(R)-(2,3-dimethoxyphenyl)(1-(2-(4-fluorophenyl)ethyl)piperidin-4-yl)methanol;4-piperidinemethanol, alpha-(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)-, (alpha-R)-;alpha-(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenylethyl))-4-piperidine methanol;M100907;MDL 100,907;MDL 100105;MDL 100907;MDL-100,907;MDL-100907;MDL100105;volinanserin

Chemical Property of Volinanserin

Chemical Property:

• Vapor Pressure: 8.6E-11mmHg at 25°C
• Melting Point: 89-91°C
• Boiling Point: 499.4°Cat760mmHg
• Flash Point: 255.8°C
• PSA: 41.93000
• Density: 1.15g/cm³
• LogP: 3.76890
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 373.20532192
• Heavy Atom Count: 27
• Complexity: 422

Purity/Quality:

98%,99%, ^*data from raw suppliers

MDL 100907 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC(=C1OC)C(C2CCN(CC2)CCC3=CC=C(C=C3)F)O
• Isomeric SMILES: COC1=CC=CC(=C1OC)[C@@H](C2CCN(CC2)CCC3=CC=C(C=C3)F)O
• Recent ClinicalTrials: Efficacy and Safety of Volinanserin on Sleep Maintenance Insomnia - Polysomnographic Study
• Recent EU Clinical Trials: Comparison of the safety and efficacy of volinanserin and lormetazepam in the treatment of insomnia characterized by sleep maintenance difficulties. A 4 week, randomized, double-blind, double-dummy, comparative, parallel-group study.
• Description: Volinanserin is a potent and selective antagonist of the serotonin receptor 5-HT2A (Ki = 0.36-0.85 nM). It weakly binds 5-HT2C, α1-adrenergic, and sigma receptors (Ki = 88, 128, and 87 nM) and much less effectively associates with other serotonin, dopamine, adrenergic, muscarinic acetylcholine receptors and monoamine transporters. Volinanserin displays antipsychotic activity, attenuates impulsivity, and augments antidepressant effects in vivo.
• Uses: As a serotonin 5-HT2A receptor antagonist, Volinanserin Hydrochloride Salt can be used as potential controls in various biological studies. Volinanserin is a serotonin receptor 5-HT2A antagonist; anti-psychotic.

Technology Process of Volinanserin

There total 38 articles about Volinanserin 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: 99.9%

Candida cylindracea lipase + α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, butyrate ester (243640-22-4) → R-(+)-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol (139290-65-6)

Guidance literature:

In methanol; t-BuOMe; dichloromethane; ethyl acetate;

Reference yield: 95.0%

(2-bromoethyl)-4-fluorobenzene (332-42-3) + (2,3‐dimethoxyphenyl)(piperidine‐4‐yl)methanol (243640-19-9) → R-(+)-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol (139290-65-6)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 85 ℃; for 1.5h;

DOI:10.1016/S0968-0896(00)00175-9

Reference yield: 83.1%

(R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid salt (243640-20-2) → (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid, potassium salt + R-(+)-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol (139290-65-6)

Guidance literature:

With potassium carbonate; In water; toluene; at 18 - 60 ℃; for 0.5 - 1.5h; Product distribution / selectivity;

upstream raw materials:

α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, butyrate ester

(R)-(+)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone

methyl iodide

diazomethane

Downstream raw materials:

(R)-(+)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone

Refernces

• 1、 King, Chi-Hsin R.,Margolin, Alexey L.. "Immobilization of Substrates in Enzyme-Catalyzed Hydrolysis". . p. 943 - 946. Retrieved 1993.
• 2、 Morris, David J.,Hayes, Aidan M.,Wills, Martin. "The "reverse-tethered" ruthenium (II) catalyst for asymmetric transfer hydrogenation: Further applications". . p. 7035 - 7044. Retrieved 2007/10/03.