• Name

  metopimazine

• EINECS 237-818-4
• CAS No. 14008-44-7
• Article Data4
• CAS DataBase
• Density 1.293g/cm³
• Solubility
• Melting Point 170.5℃
• Formula C22H27 N3 O3 S2
• Boiling Point 721.2°Cat760mmHg
• Molecular Weight 445.607
• Flash Point 390°C
• Transport Information
• Appearance
• Safety Poison by intravenous, intraperitoneal, and subcutaneous routes. Moderately toxic by ingestion. An anti-emetic agent. When heated to decomposition it emits very toxic fumes of SO_x and NO_x.
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Isonipecotamide,1-[3-[2-(methylsulfonyl)phenothiazin-10-yl]propyl]- (7CI,8CI);1-[3-[2-(Methylsulfonyl)phenothiazin-10-yl]propyl]-4-piperidinecarboxamide;1-[3-[2-(Methylsulfonyl)phenothiazin-10-yl]propyl]isonipecotamide;2-Methylsulfonyl-10-[3-(4-carbamoylpiperidino)propyl]phenothiazine;EXP 999;Metopimazine;RP 9965;Vogalene;? Metopimazine;
• PSA 117.39000
• LogP 5.06420

Synthetic route

39546-32-2

4-carboxamidopiperidine

40051-30-7

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

14008-44-7

metopimazine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 90 - 100℃; for 8h; Temperature; Reagent/catalyst; Solvent;	65%

129846-94-2

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

14008-44-7

metopimazine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 6h;	25%
Multi-step reaction with 4 steps 1: sodium hydride / dimethyl sulfoxide / 4 h / 90 °C 2: potassium hydroxide / acetone / 3 h / 50 °C 3: hydrogenchloride / acetone; water / 6 h / 0 - 20 °C 4: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 5 h / 0 °C View Scheme

129846-91-9

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

14008-44-7

metopimazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / 99percent N2H4*H2O, FeCl3*6H2O, active carbon / ethanol / 10 h / Heating 2: 25 percent / 80percent NaOH / dimethylformamide / 6 h / 100 °C View Scheme
Multi-step reaction with 5 steps 1: iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate / ethanol / 2 h / 80 °C 2: sodium hydride / dimethyl sulfoxide / 4 h / 90 °C 3: potassium hydroxide / acetone / 3 h / 50 °C 4: hydrogenchloride / acetone; water / 6 h / 0 - 20 °C 5: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 5 h / 0 °C View Scheme

23503-69-7

1-[2-(methylsulfanyl)-10H-phenothiazin-10-yl]ethanone

14008-44-7

metopimazine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxone / water; N,N-dimethyl-formamide / 3 h / 20 - 30 °C 2.1: potassium hydroxide / acetone / 20 - 30 °C 2.2: 3 h / 20 - 60 °C 3.1: potassium carbonate / toluene; N,N-dimethyl-formamide / 8 h / 90 - 100 °C View Scheme
Multi-step reaction with 3 steps 1.1: oxone / acetonitrile; water / 2 h / 20 - 30 °C / Large scale; Green chemistry 1.2: 3 h / 60 - 70 °C / Large scale; Green chemistry 2.1: potassium hydroxide / acetone / 20 - 30 °C 2.2: 3 h / 20 - 60 °C 3.1: potassium carbonate / toluene; N,N-dimethyl-formamide / 8 h / 90 - 100 °C View Scheme
Multi-step reaction with 3 steps 1.1: oxone; tetrabutylammomium bromide / water; dichloromethane / 6 h / 30 - 40 °C 2.1: potassium hydroxide / acetone / 20 - 30 °C 2.2: 3 h / 20 - 60 °C 3.1: potassium carbonate / toluene; N,N-dimethyl-formamide / 8 h / 90 - 100 °C View Scheme

7643-08-5

2-(methylthio)-10H-phenothiazine

14008-44-7

metopimazine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene / 1 h / 20 - 30 °C 2.1: oxone / water; N,N-dimethyl-formamide / 3 h / 20 - 30 °C 3.1: potassium hydroxide / acetone / 20 - 30 °C 3.2: 3 h / 20 - 60 °C 4.1: potassium carbonate / toluene; N,N-dimethyl-formamide / 8 h / 90 - 100 °C View Scheme
Multi-step reaction with 4 steps 1.1: toluene / 1 h / 20 - 30 °C 2.1: oxone / acetonitrile; water / 2 h / 20 - 30 °C / Large scale; Green chemistry 2.2: 3 h / 60 - 70 °C / Large scale; Green chemistry 3.1: potassium hydroxide / acetone / 20 - 30 °C 3.2: 3 h / 20 - 60 °C 4.1: potassium carbonate / toluene; N,N-dimethyl-formamide / 8 h / 90 - 100 °C View Scheme
Multi-step reaction with 4 steps 1.1: toluene / 1 h / 20 - 30 °C 2.1: oxone; tetrabutylammomium bromide / water; dichloromethane / 6 h / 30 - 40 °C 3.1: potassium hydroxide / acetone / 20 - 30 °C 3.2: 3 h / 20 - 60 °C 4.1: potassium carbonate / toluene; N,N-dimethyl-formamide / 8 h / 90 - 100 °C View Scheme

1-[2-(methylsulfonyl)-10H-phenothiazin-10-yl]ethanone

14008-44-7

metopimazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide / acetone / 20 - 30 °C 1.2: 3 h / 20 - 60 °C 2.1: potassium carbonate / toluene; N,N-dimethyl-formamide / 8 h / 90 - 100 °C View Scheme

39546-32-2

4-carboxamidopiperidine

C16H15NO3S2

14008-44-7

metopimazine

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0℃; for 5h;	117 g

97-07-4

1-chloro-4-methanesulfonyl-2-nitrobenzene

14008-44-7

metopimazine

Conditions

Conditions

Yield

Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 4 h / 20 °C 2: iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate / ethanol / 2 h / 80 °C 3: sodium hydride / dimethyl sulfoxide / 4 h / 90 °C 4: potassium hydroxide / acetone / 3 h / 50 °C 5: hydrogenchloride / acetone; water / 6 h / 0 - 20 °C 6: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 5 h / 0 °C View Scheme

2557-78-0

2-fluorothiophenol

14008-44-7

metopimazine

Conditions

Conditions

Yield

Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 4 h / 20 °C 2: iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate / ethanol / 2 h / 80 °C 3: sodium hydride / dimethyl sulfoxide / 4 h / 90 °C 4: potassium hydroxide / acetone / 3 h / 50 °C 5: hydrogenchloride / acetone; water / 6 h / 0 - 20 °C 6: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 5 h / 0 °C View Scheme

23503-68-6

2-(methylsulfonyl)-10H-phenothiazine

14008-44-7

metopimazine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / acetone / 3 h / 50 °C 2: hydrogenchloride / acetone; water / 6 h / 0 - 20 °C 3: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 5 h / 0 °C View Scheme

75-75-2

methanesulfonic acid

14008-44-7

metopimazine

1-(3-(2-(methylsulfonyl)-10H-phenothiazin-10-yl)propyl)piperidine-4-carboxamide methanesulfonic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20 - 25℃; for 0.5h; Time; Large scale;	85%

14008-44-7

metopimazine

18182-00-8

1-(3-[2-(methylsulfonyl)-10H-phenothiazin-10-yl]propyl)-4-piperidine carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 70 - 80℃; for 10h;

Metopimazine Chemical Properties

Metopimazine Toxicity Data With Reference

Metopimazine Safety Profile