Product Name

  • Name

    Chlorpromazine

  • EINECS 200-045-8
  • CAS No. 50-53-3
  • Article Data36
  • CAS DataBase
  • Density 1.212g/cm3
  • Solubility Soluble
  • Hazard Symbols 6.1 (Packing Group: III) UN NO.
  • Synonyms Phenothiazine,2-chloro-10-[3-(dimethylamino)propyl]- (7CI,8CI);2-Chloro-10-[3-(dimethylamino)propyl]phenothiazine; 2-Chloropromazine; 2601A;Aminazin; Aminazine; Ampliactil; Amplictil; BC 135; CPZ; Chlor-Promanyl;Chlordelazin; Chlorderazin; Chlorpromados; Chlorpromazine; Chlropromados;Contomin; Elmarin; Esmind; Fenactil; Fenaktyl; Fraction AB; HL 5746;Largactilothiazine; Largactyl; Megaphen; NSC 167745; NSC 226514; Noiafren;Novomazina; Phenactyl; Proma; Promactil; Promazil; Propaphenin; Prozil; RP4560; SKF 2601A; Sanopron; Sedatil; Thorazin; Thorazine; Wintermin
  • PSA 31.78000
  • LogP 4.95940

Synthetic route

C11H16ClIN2
1219602-20-6

C11H16ClIN2

2-bromothiophenol
6320-02-1

2-bromothiophenol

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; L-proline In ethyl methyl ether at 90 - 110℃; Inert atmosphere;78%
formaldehyd
50-00-0

formaldehyd

2-chloro-10-(3-aminopropyl)phenothiazine
2095-17-2

2-chloro-10-(3-aminopropyl)phenothiazine

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With formic acid In water at 80℃; for 8h; Eschweiler-Clark Amine Methylation; Microwave irradiation;66%
2-bromo-4-chloroiodobenzene
31928-44-6

2-bromo-4-chloroiodobenzene

2-bromothiophenol
6320-02-1

2-bromothiophenol

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 60 - 160℃; for 2.33333h; Microwave irradiation;50%
2-chlorophenothiazine
92-39-7

2-chlorophenothiazine

3-(Dimethylamino)propyl chloride
109-54-6

3-(Dimethylamino)propyl chloride

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With sodium amide
(i) NaNH2, toluene, (ii) /BRN= 605294/; Multistep reaction;
With potassium hydroxide; potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate toluene 1.) room temp., 2 h, 2.) reflux, 18 h; Yield given. Multistep reaction;
3-Dimethylamino-1-propanol
3179-63-3

3-Dimethylamino-1-propanol

2-chloro-phenothiazine-10-carbonyl chloride
36798-98-8

2-chloro-phenothiazine-10-carbonyl chloride

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With toluene Erhitzen des Reaktionsprodukts unter vermindertem Druck auf 210-220grad;
3-(2-chloro-10H-phenothiazin-10-yl)propanonitrile
4414-83-9

3-(2-chloro-10H-phenothiazin-10-yl)propanonitrile

A

2-chloro-10-(3-aminopropyl)phenothiazine
2095-17-2

2-chloro-10-(3-aminopropyl)phenothiazine

B

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With nickel; dimethyl amine; benzene at 110 - 116℃; under 58840.6 Torr; Hydrogenation;
N'-[2-(2-bromo-phenylsulfanyl)-5-chloro-phenyl]-N,N-dimethyl-propanediyldiamine
109454-48-0

N'-[2-(2-bromo-phenylsulfanyl)-5-chloro-phenyl]-N,N-dimethyl-propanediyldiamine

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With copper; potassium carbonate; N,N-dimethyl-formamide
chlorpromazine sulfoxide
969-99-3

chlorpromazine sulfoxide

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With iron; acetic acid; xylene
1-(2-chloro-phenothiazin-10-yl)-3-methanesulfonyloxy-propane
41951-57-9

1-(2-chloro-phenothiazin-10-yl)-3-methanesulfonyloxy-propane

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With dimethyl amine
bis-[3-(2-chloro-phenothiazin-10-yl)-propyl]-methyl-amine
103278-35-9

bis-[3-(2-chloro-phenothiazin-10-yl)-propyl]-methyl-amine

A

10-Allyl-2-chlorophenothiazine
63615-79-2

10-Allyl-2-chlorophenothiazine

B

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With sodium hydroxide; methyl iodide
2-chloro-10-(3-chloropropyl)-10H-phenothiazine
2765-59-5

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

dimethyl amine
124-40-3

dimethyl amine

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
In ethanol
dopamine
51-61-6

dopamine

chloropromazine cation radical
50-53-3

chloropromazine cation radical

A

dopaminoquinone
50673-96-6

dopaminoquinone

B

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
In hydrogenchloride Rate constant; pH=1.5;
2-chlorophenothiazine
92-39-7

2-chlorophenothiazine

3-(Dimethylamino)propyl chloride
109-54-6

3-(Dimethylamino)propyl chloride

A

2-chloro-10-methyl-10H-phenothiazine
19607-03-5

2-chloro-10-methyl-10H-phenothiazine

B

10-Allyl-2-chlorophenothiazine
63615-79-2

10-Allyl-2-chlorophenothiazine

C

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With sodium hydroxide In chlorobenzene; toluene for 4.5h; Heating; Yield given. Yields of byproduct given;
carbon dioxide
124-38-9

carbon dioxide

2-chloro-10-<3-N-trimethylsilyl, 3-N-methylaminopropyl> phenothiazine

2-chloro-10-<3-N-trimethylsilyl, 3-N-methylaminopropyl> phenothiazine

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride 1.) THF, -45 deg C - 60 deg C, 2.) 60 deg C, 10 min; Yield given. Multistep reaction;
Norepinephrine
138-65-8

Norepinephrine

chloropromazine cation radical
50-53-3

chloropromazine cation radical

A

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

B

4-(2-Amino-1-hydroxy-ethyl)-[1,2]benzoquinone
14309-96-7

4-(2-Amino-1-hydroxy-ethyl)-[1,2]benzoquinone

Conditions
ConditionsYield
In hydrogenchloride Rate constant; pH=7;
Epinephrine
329-65-7

Epinephrine

chloropromazine cation radical
50-53-3

chloropromazine cation radical

A

adrenaline o-quinone
672-73-1, 162706-73-2

adrenaline o-quinone

B

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
In hydrogenchloride Rate constant; pH=7;
aminopyrine
58-15-1

aminopyrine

chlorpromazine semiquinone cation radical

chlorpromazine semiquinone cation radical

A

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

B

aminopyrine radical cation
58-15-1

aminopyrine radical cation

Conditions
ConditionsYield
Rate constant; pH 6;
[3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-(2-methyl-acryloyloxymethyl)-ammonium; chloride
76637-15-5

[3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-(2-methyl-acryloyloxymethyl)-ammonium; chloride

A

formaldehyd
50-00-0

formaldehyd

B

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

C

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
In water at 21℃; pH=8.8, ionic strength 0.1 M KCl; other pH, other temp.; hydrolysis rate;
Benzoyloxymethyl-[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-ammonium; chloride
76637-14-4

Benzoyloxymethyl-[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-ammonium; chloride

A

formaldehyd
50-00-0

formaldehyd

B

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
In water at 21℃; pH=8.2, ionic strength 0.1 M KCl; other pH; hydrolysis rate;
dopamine
51-61-6

dopamine

chlorpromazine semiquinone cation radical

chlorpromazine semiquinone cation radical

A

dopaminoquinone
50673-96-6

dopaminoquinone

B

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
Kinetics; Rate constant; in constant ionic strength (0.8 M) mixtures of HClO4 and NaClO4 in 40percent MeO/H2O (w/w) with a pH between 0.1 and 1.5;
chloropromazine cation radical
50-53-3

chloropromazine cation radical

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

A

4-methylbenzo-1,2-quinone
3131-54-2

4-methylbenzo-1,2-quinone

B

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
In hydrogenchloride Rate constant; pH=7;
benzyl-<3-(2-chloro-phenothiazin-10-yl)-propyl>-dimethyl-ammonium-methanesulfonate

benzyl-<3-(2-chloro-phenothiazin-10-yl)-propyl>-dimethyl-ammonium-methanesulfonate

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With palladium on activated charcoal; acetic acid Hydrogenation;
2-chlorophenothiazine
92-39-7

2-chlorophenothiazine

methanesulfonic acid-<3-dimethylamino-propyl ester

methanesulfonic acid-<3-dimethylamino-propyl ester

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With n-butyllithium; diethyl ether
2-chlorophenothiazine
92-39-7

2-chlorophenothiazine

toluene-4-sulfonic acid-<3-dimethylamino-propyl ester>-hydrochloride

toluene-4-sulfonic acid-<3-dimethylamino-propyl ester>-hydrochloride

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
With xylene
2-chloro-N-methyl-10H-phenothiazine-10-propanamine hydrochloride
3953-65-9

2-chloro-N-methyl-10H-phenothiazine-10-propanamine hydrochloride

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (NH4)2SO4 / 110 °C
2: 2.) LiAlH4 / 1.) THF, -45 deg C - 60 deg C, 2.) 60 deg C, 10 min
View Scheme
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous H2O2; ethanol
2: iron-powder; acetic acid; xylene
View Scheme
With potassium carbonate In water pH=10; Inert atmosphere;
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

tert-butyl (2-(2-((4-(chloromethyl)benzyl)oxy)ethoxy)ethyl)carbamate

tert-butyl (2-(2-((4-(chloromethyl)benzyl)oxy)ethoxy)ethyl)carbamate

3-(2-chloro-10H-phenothiazin-10-yl)-N-(4-(11,11-dimethyl-9-oxo-2,5,10-trioxa-8-azadodecyl)benzyl)-N,N-dimethylpropan-1-aminium chloride

3-(2-chloro-10H-phenothiazin-10-yl)-N-(4-(11,11-dimethyl-9-oxo-2,5,10-trioxa-8-azadodecyl)benzyl)-N,N-dimethylpropan-1-aminium chloride

Conditions
ConditionsYield
In acetone at 40℃; for 48h; Inert atmosphere; Reflux;97%
2-aminopyridine
504-29-0

2-aminopyridine

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

10-(3-(dimethylamino)propyl)-N-(pyridin-2-yl)-10H-phenothiazin-2-amine

10-(3-(dimethylamino)propyl)-N-(pyridin-2-yl)-10H-phenothiazin-2-amine

Conditions
ConditionsYield
With methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II); potassium hydroxide In water; toluene at 110℃; Flow reactor;95%
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

chlorpromazine semiquinone cation radical

chlorpromazine semiquinone cation radical

Conditions
ConditionsYield
With GLUTATHIONE; isopropyl alcohol; acetone In water Rate constant; Product distribution; Irradiation; pH=3; pulse radiolysis; other thiol reagents and CPZ concentrations;91%
With halothane peroxyl radical In various solvent(s) Rate constant; Ambient temperature; Irradiation; pH=7; pulse radiolysis; different CZ concentrations;54 % Spectr.
With dihydrogen peroxide; horseradish peroxidase In acetate buffer pH=4.5; Kinetics; Further Variations:; Reagents; Oxidation;
With hydroxyl pH=7; Kinetics; aq. phosphate buffer;
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-ol
3926-64-5

10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-ol

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 14h; Schlenk technique; Inert atmosphere;87%
With water for 120h; Irradiation;
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

chlorpromazine sulfoxide
969-99-3

chlorpromazine sulfoxide

Conditions
ConditionsYield
In acetonitrile Electrolysis;83%
With hydrogenchloride; sodium nitrite In water for 2h; Product distribution; oxidation of phenothiazine salts to their sulfoxides with aqueous nitrous acid; hydrogen peroxide oxidation;74%
With hydrogenchloride; sodium nitrite In water for 2h;74%
chloromethyl benzoate
5335-05-7

chloromethyl benzoate

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Benzoyloxymethyl-[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-ammonium; chloride
76637-14-4

Benzoyloxymethyl-[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-ammonium; chloride

Conditions
ConditionsYield
In acetone81.5%
carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

2-chloro-N-(1-chloroethoxycarbonyl)-N-methyl-10H-phenothiazine-10-propanamine

2-chloro-N-(1-chloroethoxycarbonyl)-N-methyl-10H-phenothiazine-10-propanamine

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 1h; Substitution; Heating;81%
Chloromethyl methacrylate
27550-73-8

Chloromethyl methacrylate

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

[3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-(2-methyl-acryloyloxymethyl)-ammonium; chloride
76637-15-5

[3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-(2-methyl-acryloyloxymethyl)-ammonium; chloride

Conditions
ConditionsYield
In acetone79%
indole
120-72-9

indole

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

3-(2-(1H-indol-3-yl)-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine

3-(2-(1H-indol-3-yl)-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine

Conditions
ConditionsYield
With Cy-DHTP*HBF4; palladium diacetate; lithium tert-butoxide In toluene at 20 - 110℃; for 21h; Inert atmosphere; Sealed tube;65%
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester
21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

chlorpromazine N+-glucuronide chloride
86492-49-1

chlorpromazine N+-glucuronide chloride

Conditions
ConditionsYield
With XAD-2 ion-exchange resin; sodium hydrogencarbonate In water; benzene for 72h; Ambient temperature;46%
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester
21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

A

chlorpromazine N+-glucuronide chloride
86492-49-1

chlorpromazine N+-glucuronide chloride

B

[3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-methoxycarbonyl-tetrahydro-pyran-2-yl)-ammonium; bromide
145823-11-6

[3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-methoxycarbonyl-tetrahydro-pyran-2-yl)-ammonium; bromide

C

Hydrogen carbonate[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-carboxy-tetrahydro-pyran-2-yl)-ammonium;
145823-13-8

Hydrogen carbonate[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-carboxy-tetrahydro-pyran-2-yl)-ammonium;

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; benzene for 72h; Ambient temperature;A 46%
B n/a
C n/a
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

A

Chlorpromazine oxide
1672-76-0

Chlorpromazine oxide

B

chlorpromazine sulfoxide
969-99-3

chlorpromazine sulfoxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid; sodium hydroxide In dichloromethane at 0℃; for 4h;A 40%
B 10%
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

A

7-hydroxychlorpromazine
2095-62-7

7-hydroxychlorpromazine

B

2-chloro-10-(3-dimethylamino-propyl)-10H-phenothiazin-1-ol
3926-66-7

2-chloro-10-(3-dimethylamino-propyl)-10H-phenothiazin-1-ol

C

3-hydroxyl CPZ
3930-47-0

3-hydroxyl CPZ

D

chlorpromazine sulfoxide
969-99-3

chlorpromazine sulfoxide

Conditions
ConditionsYield
Stage #1: 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine With ethylenediaminetetraacetic acid trisodium salt; oxygen; manganese (II) acetate tetrahydrate; ascorbic acid In water pH=4; Udenfriend reaction;
Stage #2: With ferrous(II) sulfate heptahydrate; ethylenediaminetetraacetic acid trisodium salt; oxygen In water at 45℃; for 2h; Udenfriend reaction;
A n/a
B 0.4%
C 0.84%
D 0.58%
2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

chlorpromazine N',S-dioxide
10404-90-7

chlorpromazine N',S-dioxide

Conditions
ConditionsYield
With ethanol; dihydrogen peroxide
With dihydrogen peroxide In ethanol
With dihydrogen peroxide In ethanol for 24h; Ambient temperature;
Multi-step reaction with 2 steps
1: aq. H2O2, NH3 / ethanol / 60 h
2: aq. H2O2 / ethanol / 84 h
View Scheme
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid; sodium hydroxide / dichloromethane / 4 h / 0 °C
2: 3-chloro-benzenecarboperoxoic acid; sodium hydroxide / dichloromethane / 4 h / 0 °C
View Scheme
9-(bromomethyl)acridine
1556-34-9

9-(bromomethyl)acridine

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

acridin-9-ylmethyl-[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-ammonium; bromide
56265-45-3

acridin-9-ylmethyl-[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-ammonium; bromide

Conditions
ConditionsYield
In acetonitrile Ambient temperature;
2-bromo-1-phenyl-ethanone oxime
14181-72-7, 17082-13-2, 17082-14-3

2-bromo-1-phenyl-ethanone oxime

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
50-53-3

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

[3-(2-chloro-phenothiazin-10-yl)-propyl]-(2-hydroxyimino-2-phenyl-ethyl)-dimethyl-ammonium; bromide
19337-44-1

[3-(2-chloro-phenothiazin-10-yl)-propyl]-(2-hydroxyimino-2-phenyl-ethyl)-dimethyl-ammonium; bromide

Conditions
ConditionsYield
In diethyl ether

Chlorpromazine Chemical Properties

MF: C17H19ClN2S
MW: 318.86416
MS:
EINECS: 200-045-8
Product Categories: 
Mol File: 50-53-3.mol
Surface Tension: 46.6 dyne/cm 
Density: 1.212 g/cm3 
Flash Point: 226 °C 
Enthalpy of Vaporization: 70.89 kJ/mol 
Boiling Point: 450.1 °C at 760 mmHg 
Vapour Pressure: 2.72E-08 mmHg at 25°C  
 

Chlorpromazine Uses

3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine(50-53-3) have good effect on have good effect on schizophrenia, severe depression and anxiety, hyperactive children, you can also use 3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine(50-53-3) to relieve nausea, belching.

Chlorpromazine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous > 10mg/kg (10mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
 
cat LDLo oral 100mg/kg (100mg/kg) behavioral: altered sleep time (including change in righting reflex)
behavioral: regidity
gastrointestinal: nausea or vomiting
 
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
child LDLo oral 37500ug/kg (37.5mg/kg) behavioral: convulsions or effect on seizure threshold
behavioral: coma
 
New England Journal of Medicine. Vol. 256, Pg. 527, 1957.
dog LD50 intravenous 30mg/kg (30mg/kg) ungs, thorax, or respiration: emphysema
blood: hemorrhage
lungs, thorax, or respiration: acute pulmona
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 118, Pg. 358, 1959.
 
dog LD50 subcutaneous > 20mg/kg (20mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
 
dog LDLo oral 250mg/kg (250mg/kg) behavioral: altered sleep time (including change in righting reflex)
behavioral: regidity
gastrointestinal: nausea or vomiting
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
guinea pig LD50 intraperitoneal 87mg/kg (87mg/kg)   Medicina Experimentalis. Vol. 8, Pg. 237, 1963.
guinea pig LDLo oral 250mg/kg (250mg/kg) behavioral: altered sleep time (including change in righting reflex)
behavioral: regidity
gastrointestinal: nausea or vomiting
 
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
human TDLo oral 8570ug/kg/12D (8.57mg/kg) behavioral: wakefulness
behavioral: muscle weakness
 behavioral: tremor
 
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 93, 1972.
 
infant TDLo oral 20mg/kg (20mg/kg) vascular: bp lowering not characterized in autonomic section
 behavioral: somnolence (general depressed activity)
 
American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976.
 
mammal (species unspecified) LD50 oral 500mg/kg (500mg/kg) behavioral: anticonvulsant
 behavioral: alteration of classical conditioning
 
Journal of Medicinal Chemistry. Vol. 8, Pg. 836, 1965.
man TDLo oral 8900ug/kg (8.9mg/kg) lungs, thorax, or respiration: dyspnea
 
American Journal of Emergency Medicine. Vol. 14, Pg. 467, 1996.
 
man TDLo oral 217mg/kg/19D (217mg/kg) blood: agranulocytosis
skin and appendages (skin): "dermatitis, allergic: after systemic exposure"
 
Journal of Clinical Psychiatry. Vol. 46, Pg. 341, 1985.
 
monkey LD50 subcutaneous > 5mg/kg (5mg/kg)

 blood: agranulocytosis
skin and appendages (skin): "dermatitis, allergic: after systemic exposure"

 

Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
 
mouse LC50 inhalation 209mg/m3/2H (209mg/m3)
behavioral: muscle weakness
cardiac: pulse rate increase without fall in bp
blood: leukopenia
 
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 10, Pg. 73, 1968.
mouse LD50 intraperitoneal 14mg/kg (14mg/kg)   Farmaco, Edizione Scientifica. Vol. 14, Pg. 269, 1959.
mouse LD50 intravenous 16mg/kg (16mg/kg)

behavioral: muscle weakness

cardiac: pulse rate increase without fall in bp

blood: leukopenia

Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
 
mouse LD50 oral 135mg/kg (135mg/kg) lbehavioral: convulsions or effect on seizure threshold
lungs, thorax, or respiration: other changes
 
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 118, Pg. 358, 1959.
 
mouse LD50 subcutaneous 33mg/kg (33mg/kg) behavioral: ataxia
behavioral: regidity
 
Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
 
mouse LD50 unreported 82500ug/kg (82.5mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
mouse LDLo intramuscular 300mg/kg (300mg/kg)   Therapie. Vol. 15, Pg. 1064, 1960.
rabbit LD50 intravenous 16mg/kg (16mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 120, Pg. 450, 1959.
 
rat LC50 inhalation 209mg/m3/2H (209mg/m3) behavioral: muscle weakness
cardiac: pulse rate increase without fall in bp
blood: leukopenia
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 10, Pg. 73, 1968.
rat LD50 intraperitoneal 137mg/kg (137mg/kg)   German Offenlegungsschrift Patent Document. Vol. #2350222,
rat LD50 intravenous 23mg/kg (23mg/kg)  behavioral: muscle weakness
cardiac: pulse rate increase without fall in bp
blood: leukopenia
 
Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
 
rat LD50 oral 142mg/kg (142mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 261, 1968.
 
rat LD50 subcutaneous 75mg/kg (75mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 377, 1960.
women TDLo oral 200ug/kg (0.2mg/kg) behavioral: sleep
liver: "jaundice, other or unclassified"
New York State Journal of Medicine. Vol. 57, Pg. 1922, 1957.
 
women TDLo oral 16800ug/kg/3W (16.8mg/kg) blood: agranulocytosis Postgraduate Medical Journal. Vol. 69, Pg. 885, 1993.
 
women TDLo oral 166mg/kg/18D- (166mg/kg) blood: other hemolysis with or without anemia
blood: other changes
Postgraduate Medical Journal. Vol. 53, Pg. 278, 1977.
 
women TDLo oral 240mg/kg/30D- (240mg/kg) blood: agranulocytosis
blood: changes in leucocyte (wbc) count
blood: agranulocytosis
Journal of Clinical Psychiatry. Vol. 46, Pg. 341, 1985.
 
women TDLo oral 240mg/kg/30D (240mg/kg)
skin and appendages (skin): "dermatitis, allergic: after systemic exposure"
 
Journal of Clinical Psychiatry. Vol. 46, Pg. 341, 1985.
 

Chlorpromazine Specification

IUPAC: 3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine(50-53-3)
CAS: 50-53-3
Synonyms: 10H-Phenothiazine-10-propanamine, 2-chloro-N,N-dimethyl-;2601-A;2-Chloro-10-[3-(dimethyamino)propyl]phenothiazine;2-Chloropromazine;2-Cloro-10 (3-dimetilaminopropil)fenotiazina;3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine;4560 R.P.;Aminasine
 

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