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metopimazine

metopimazine Basic information
Product Name:metopimazine
Synonyms:metopimazine;1-[3-[2-[Methylsulfonyl] phenothiazin-10-yl] propyl] isonipecotamide;1-[3-(2-Methylsulfonyl-10H-phenothiazin-10-yl)propyl]-4-piperidinecarboxamide;9965 RP;EXP 999;RP-9965;Vogalene;1-[3-[2-(Methylsulfonyl)-10H-phenothiazin-10-yl]propyl]piperidin-4-carboxaMide
CAS:14008-44-7
MF:C22H27N3O3S2
MW:445.59808
EINECS:2378184
Product Categories:Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Isotope Labelled Compounds
Mol File:14008-44-7.mol
metopimazine Structure
metopimazine Chemical Properties
Melting point 170.5℃
Boiling point 721.2±60.0 °C(Predicted)
density 1.1920 (rough estimate)
refractive index 1.6320 (estimate)
storage temp. Refrigerator
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka16.44±0.20(Predicted)
color Pale Yellow
CAS DataBase Reference14008-44-7
Safety Information
ToxicityLD50 in male rats (mg/kg): 976 orally, 1080 s.c. (Goldenthal)
MSDS Information
metopimazine Usage And Synthesis
Chemical PropertiesPale Yellow Solid
OriginatorNortrip,Rhodia
UsesMetopimazine (MPZ) is used to prevent emesis during chemotherapies. Antiemetic.
Usesmetopimazine is used to prevent emesis during chemotherapies.
DefinitionChEBI: Metopimazine is a member of phenothiazines.
Manufacturing Process2-Methylsulfonyl-10-(3-chloropropyl)phenothiazine was prepared by condensation of 1-bromo-3-chloropropane and 2-methylsulfonyl phenothiazine in liquid ammonia in presence of obtained in situ sodium amide.
10 g 2-methylsulfonyl-10-(3-chloropropyl)-phenothiazine, 4 g piperidine-4- carboxylic acid amide, 3.5 g dry sodium carbonate in 200 ml of ethanol was heated to reflux for 24 hours. Than 1.75 g sodium carbonate was added and the mixture was heated another 8 hours. After that the new 1.75 g portion of sodium carbonate was added and heated for 16 hours. The solvent was removed in vacuum (20 mm Hg). The residue was stirred with 50 ml water and 150 ml ethyl acetate. The organic layer was separated and extracted with 200 ml 1 N hydrochloric acid. The water layer was made alkaline with 4 N sodium hydroxide, extracted with ethyl acetate and dried over sodium sulfate. The solvent was removed in vacuum (20 mm Hg) to dryness. The obtained residue 2-methylsulfonyl-10-(3-(4-carbamoylpiperidino)propyl)phenothiazine was recrystallized from ethyl acetate. Yield 6 g; MP: 170°-171°C.
Therapeutic FunctionAntiemetic
metopimazine Preparation Products And Raw materials
Raw materialsAmmonia-->1-Bromo-3-chloropropane-->Sodium-->Hexahydroisonicotinamide-->2-(methylsulphonyl)-10H-phenothiazine
Phloroglucinol Tropisetron ONDANSETRON FOR LC SYSTEM SUITABILITY Cetirizine hydrochloride Stugeron metopimazine 1-(3-AMINO-PROPYL)-PIPERIDINE-4-CARBOXYLIC ACID AMIDE 3-(4-METHYL-PIPERIDIN-1-YL)-PROPYLAMINE 2-Methylthiophenothiazine
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