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Basic Information
CAS No.: 14008-44-7
Name: metopimazine
Article Data: 4
Molecular Structure:
Molecular Structure of 14008-44-7 (metopimazine)
Formula: C22H27 N3 O3 S2
Molecular Weight: 445.607
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;
EINECS: 237-818-4
Density: 1.293g/cm3
Melting Point: 170.5℃
Boiling Point: 721.2°Cat760mmHg
Flash Point: 390°C
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 SOx and NOx.
PSA: 117.39000
LogP: 5.06420
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With potassium carbonate In N,N-dimethyl-formamide; toluene at 90 - 100℃; for 8h; Temperature; Reagent/catalyst; Solvent;65%
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ConditionsYield
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
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ConditionsYield
Multi-step reaction with 2 steps
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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
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ConditionsYield
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
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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
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Conditions
ConditionsYield
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
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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
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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
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1-[2-(methylsulfonyl)-10H-phenothiazin-10-yl]ethanone

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Conditions
ConditionsYield
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
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Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0℃; for 5h;117 g
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Conditions
ConditionsYield
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
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Multi-step reaction with 6 steps
1: potassium carbonate / acetone / 4 h / 20 °C
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4: potassium hydroxide / acetone / 3 h / 50 °C
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ConditionsYield
Multi-step reaction with 3 steps
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Chemistry

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 

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.

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 SOx and NOx.