Metopimazine

Base Information

• Chemical Name: Metopimazine
• CAS No.: 14008-44-7
• Deprecated CAS: 14170-03-7
• Molecular Formula: C22H27 N3 O3 S2
• Molecular Weight: 445.607
• Hs Code.: 2934300000
• European Community (EC) Number: 237-818-4
• UNII: 238S75V9AV
• DSSTox Substance ID: DTXSID80161224
• Nikkaji Number: J8.471I
• Wikipedia: Metopimazine
• Wikidata: Q194682
• NCI Thesaurus Code: C81497
• Pharos Ligand ID: XYDTSCB89PBU
• Metabolomics Workbench ID: 154384
• ChEMBL ID: CHEMBL398615
• Mol file: 14008-44-7.mol

Synonyms:1-(3-(2-methylsulfonylphenothiazin-10-yl) propyl)isonipecotinamide;metopimazine;metopimazine hydrochloride;Vogalene

Chemical Property of Metopimazine

Chemical Property:

• Vapor Pressure: 1.18E-20mmHg at 25°C
• Melting Point: 170.5℃
• Refractive Index: 1.626
• Boiling Point: 721.2°Cat760mmHg
• PKA: 16.44±0.20(Predicted)
• Flash Point: 390°C
• PSA: 117.39000
• Density: 1.293g/cm³
• LogP: 5.06420
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 445.14938408
• Heavy Atom Count: 30
• Complexity: 703

Purity/Quality:

98%Min ^*data from raw suppliers

Metopimazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN4CCC(CC4)C(=O)N
• Recent ClinicalTrials: NISCI - Nogo Inhibition in Spinal Cord Injury
• Uses: metopimazine is used to prevent emesis during chemotherapies. Metopimazine (MPZ) is used to prevent emesis during chemotherapies. Antiemetic.
• Therapeutic Function: Antiemetic

Technology Process of Metopimazine

There total 11 articles about Metopimazine 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: 65.0%

4-carboxamidopiperidine (39546-32-2) + 10-(3-chloropropyl)-2-(methylsulfonyl)-10H-phenothiazine (40051-30-7) → metopimazine (14008-44-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; toluene; at 90 - 100 ℃; for 8h; Temperature; Reagent/catalyst; Solvent;

DOI:10.1021/acs.oprd.7b00052

Reference yield: 25.0%

2‐(2-fluorophenylthio)-5-(methylsulfonyl)aniline (129846-94-2) → metopimazine (14008-44-7)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 100 ℃; for 6h;

Reference yield:

4-carboxamidopiperidine (39546-32-2) + C16H15NO3S2 → metopimazine (14008-44-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 0 ℃; for 5h;

upstream raw materials:

2‐(2-fluorophenylthio)-5-(methylsulfonyl)aniline

2-(2-fluorophenylthio)-5-(methylsulfonyl)nitrobenzene

4-carboxamidopiperidine

10-(3-chloropropyl)-2-(methylsulfonyl)-10H-phenothiazine

Downstream raw materials:

metopimazine acid

Refernces

• 1、 -. "New process for preparing metopimazine". . . Retrieved 2019/01/14.
• 2、 Sindelar, Karel,Holubek, Jiri,Koruna, Ivan,Hrubantova, Marta. "MODIFIED SYNTHESES OF 2-(METHYLTHIO)-10-(2-(1-METHYL-2-PIPERIDINYL)ETHYL)PHENOTHIAZINE (THIORIDAZINE) AND 1-(3-(2-(METHYLSULFONYL)-10-PHENOTHIAZINYL)PROPYL)-PIPERIDINE-4-CARBOXAMIDE (METOPIMAZINE)". . p. 1586 - 1601. Retrieved 2007/10/02.