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Name	Metopimazine	EINECS	237-818-4
CAS No.	14008-44-7	Density	1.293g/cm³
PSA	117.39000	LogP	5.06420
Solubility	N/A	Melting Point	170.5℃
Formula	C22H27 N3 O3 S2	Boiling Point	721.2°Cat760mmHg
Molecular Weight	445.607	Flash Point	390°C
Transport Information	N/A	Appearance	N/A
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	N/A
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	4

Metopimazine 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 N2H4H2O, FeCl36H2O, 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

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

Yield

: 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

Metopimazine Chemical Properties

The IUPAC name of Metopimazine (CAS NO.14008-44-7): 3-(3-Chloro-4-methoxyphenyl)-1,1-dimethylurea
Synonyms: Metopimazine;1-[3-[2-[Methylsulfonyl] phenothiazin-10-yl] propyl] isonipecotamide ; 1-[3-(2-Methylsulfonyl-10H-phenothiazin-10-yl)propyl]-4-piperidinecarboxamide ; 9965 RP ;E XP 999 ; RP-9965 ; Vogalene
CAS: 14008-44-7
EINECS: 237-818-4
Molecular Formula: C₂₂H₂₇N₃O₃S₂
Molecular Structure:

Formula Weight: 445.59808 g/mol
Index of Refraction: 1.577
Density: 1.254 g/cm³
Flash Point: 190.6 °C
Boiling Point: 391.6 °C at 760 mmHg

Metopimazine Toxicity Data With Reference

The toxicity of Metopimazine (CAS NO.14008-44-7):

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	oral	500mg/kg (500mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: TREMOR	Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
dog	LD₅₀	oral	500mg/kg (500mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: TREMOR	Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
guinea pig	LDLo	oral	250mg/kg (250mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: ATAXIA	Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
mouse	LD₅₀	intraperitoneal	78mg/kg (78mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CHANGE IN SENSATION OF SMELL: OLFACTION SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Oyo Yakuri. Pharmacometrics. Vol. 1, Pg. 97, 1967.
mouse	LD₅₀	intravenous	64mg/kg (64mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CHANGE IN SENSATION OF SMELL: OLFACTION SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Oyo Yakuri. Pharmacometrics. Vol. 1, Pg. 97, 1967.
mouse	LD₅₀	oral	800mg/kg (800mg/kg)		Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles. Vol. 266, Pg. 2365, 1968.
mouse	LD₅₀	subcutaneous	315mg/kg (315mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 32, 1972.
rabbit	LDLo	oral	2gm/kg (2000mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: ATAXIA	Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
rat	LD₅₀	oral	976mg/kg (976mg/kg)		Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat	LD₅₀	subcutaneous	1080mg/kg (1080mg/kg)		Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Metopimazine Safety Profile

The safety information of Metopimazine (CAS NO.14008-44-7):
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.

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