Caroverine

Base Information

• Chemical Name: Caroverine
• CAS No.: 23465-76-1
• Molecular Formula: C22H27 N3 O2
• Molecular Weight: 365.475
• Hs Code.: 2933990090
• European Community (EC) Number: 636-607-8
• UNII: XJ73B0K6KB
• DSSTox Substance ID: DTXSID6049010
• Nikkaji Number: J20.779I
• Wikipedia: Caroverine
• Wikidata: Q5045575
• NCI Thesaurus Code: C73173
• Metabolomics Workbench ID: 154613
• ChEMBL ID: CHEMBL1729803
• Mol file: 23465-76-1.mol

Synonyms:caroverine;caroverine fumarate;caroverine fumarate (1:1);caroverine monohydrochloride;P-201;P-201-1;spadon;Spasmium

Chemical Property of Caroverine

Chemical Property:

• Vapor Pressure: 5.81E-11mmHg at 25°C
• Melting Point: 69°
• Boiling Point: 521.2°Cat760mmHg
• PKA: 9.52±0.25(Predicted)
• Flash Point: 269°C
• PSA: 47.36000
• Density: 1.11g/cm³
• LogP: 3.33770
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 365.21032711
• Heavy Atom Count: 27
• Complexity: 510

Purity/Quality:

98%Min ^*data from raw suppliers

Caroverine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCN1C2=CC=CC=C2N=C(C1=O)CC3=CC=C(C=C3)OC
• Recent ClinicalTrials: Caroverin and Inner Ear Diseases
• Recent EU Clinical Trials: Double blind, placebo-controlled randomized clinical trial to evaluate the efficacy and safety of a transtympanic treatment of tinnitus with caroverine
• Uses: Caroverine is a quinoxaline compound that was originally developed as a spasmolytic drug, but is now used to treat inner ear diseases such as tinnitus. Caroverine is a calcium channel blocker and is also an antiglutamatergic drug.

Technology Process of Caroverine

There total 8 articles about Caroverine 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: 90.0%

1-(2-iodoethyl)-3-(4-methoxybenzyl)quinoxalin-2(1H)-one (1610961-35-7) + diethylamine (109-89-7) → 1-[2-(diethylamino)ethyl]-3-(4-methoxybenzyl)quinoxalin-2(1H)-one (23465-76-1)

Guidance literature:

With tert-butyldimethylsilyl chloride; In dichloromethane; at 20 ℃; for 18h; Reagent/catalyst;

DOI:10.1016/j.tetlet.2014.03.061

Reference yield:

4-(2-chloroethyl)-2-(4-methoxybenzyl)-3-oxo-3,4-dihydroquinoxaline 1-oxide (1610961-27-7) → 1-[2-(diethylamino)ethyl]-3-(4-methoxybenzyl)quinoxalin-2(1H)-one (23465-76-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium dithionite / acetonitrile; water / 3 h / 20 °C

2: sodium iodide / acetone / 12 h / Reflux

3: tert-butyldimethylsilyl chloride / dichloromethane / 18 h / 20 °C

With sodium dithionite; tert-butyldimethylsilyl chloride; sodium iodide; In dichloromethane; water; acetone; acetonitrile; 2: |Finkelstein Reaction;

DOI:10.1016/j.tetlet.2014.03.061

Reference yield:

2-Anilinoethanol (122-98-5) → 1-[2-(diethylamino)ethyl]-3-(4-methoxybenzyl)quinoxalin-2(1H)-one (23465-76-1)

Guidance literature:

Multi-step reaction with 7 steps

1: thionyl chloride; N,N-dimethyl-formamide / toluene / 5 h / 0 - 80 °C / Inert atmosphere

2: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3: sodium nitrite; sulfuric acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 5 h / 0 - 20 °C

4: tetrahydrofuran / 18 h / -40 °C / Inert atmosphere

5: sodium dithionite / acetonitrile; water / 3 h / 20 °C

6: sodium iodide / acetone / 12 h / Reflux

7: tert-butyldimethylsilyl chloride / dichloromethane / 18 h / 20 °C

With thionyl chloride; sodium dithionite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sulfuric acid; tert-butyldimethylsilyl chloride; triethylamine; N,N-dimethyl-formamide; sodium iodide; sodium nitrite; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; 6: |Finkelstein Reaction;

DOI:10.1016/j.tetlet.2014.03.061

upstream raw materials:

4-(2-chloroethyl)-2-(4-methoxybenzyl)-3-oxo-3,4-dihydroquinoxaline 1-oxide

2-Anilinoethanol

1-(2-chloroethyl)-3-(4-methoxybenzyl)quinoxalin-2(1H)-one

1-(2-iodoethyl)-3-(4-methoxybenzyl)quinoxalin-2(1H)-one

Refernces