Product Name

  • Name

    Chlorpromazine hydrochloride

  • EINECS 200-701-3
  • CAS No. 69-09-0
  • Article Data3
  • CAS DataBase
  • Density 1.077 g/cm3 (15 C)
  • Solubility >=10 g/100 mL at 24 °C
  • Melting Point 192-196 °C
  • Formula C17H19ClN2S.HCl
  • Boiling Point 450.1 °C at 760 mmHg
  • Molecular Weight 355.331
  • Flash Point 226 °C
  • Transport Information UN 2811 6.1/PG 1
  • Appearance creamy white crystalline powder
  • Safety 28-36/37-45
  • Risk Codes 25-26
  • Molecular Structure Molecular Structure of 69-09-0 (Chlorpromazine hydrochloride)
  • Hazard Symbols VeryT+
  • Synonyms 10H-Phenothiazine-10-propanamine,2-chloro-N,N-dimethyl-, monohydrochloride (9CI);Phenothiazine,2-chloro-10-[3-(dimethylamino)propyl]-, monohydrochloride (8CI);2-Chloro-10-(3-dimethylaminopropyl)phenothiazine monohydrochloride;Aminazin monohydrochloride;Chloractil;Hebanil;Hibanil;Hibernal;Klorproman;Klorpromex;Largactil;Largaktyl;Marazine;Megatil;Norcozine;Promacid;Propaphen;
  • PSA 31.78000
  • LogP 5.76140

Synthetic route

2-chlorophenothiazine
92-39-7

2-chlorophenothiazine

3-(dimethylamino)propyl chloride hydrochloride
5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 at 80℃; for 1h;85%
oxovanadium(IV) sulfate

oxovanadium(IV) sulfate

chloropromazine cation radical
50-53-3

chloropromazine cation radical

A

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

B

vanadium(5+)

vanadium(5+)

Conditions
ConditionsYield
In water Kinetics; deoxygenated solutions, 25.0-38.7°C, 0.1 to 1.0 M - H(1+); not isolated, detd. by stopped-flow UV/VIS spectroscopy;
...Expand
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

chlorpromazine sulfoxide
969-99-3

chlorpromazine sulfoxide

Conditions
ConditionsYield
With oxygen; nitrogen(II) oxide In acetonitrile for 2h; -20 deg C -> room temperature;100%
With oxygen In acetonitrile for 2h; Product distribution; -20 deg C -> room temperature; aerial oxidation of various phenothiazines and related compounds catalysed by nitrogen oxides, possible mechanism, intermediate cation radicals;100%
With ethanol; dihydrogen peroxide
water
7732-18-5

water

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

potassium hexacyanoferrate(III)

potassium hexacyanoferrate(III)

chlorpromazinium ferricyanide monohydrate

chlorpromazinium ferricyanide monohydrate

Conditions
ConditionsYield
In water E-2 M solns. were mixed; ppt. was filtered, thoroughly washed with distd. water, dried at room temp., elem. anal.;99.5%
...Expand
ammonium tetrathiocyanodiamminochromate(III) monohydrate

ammonium tetrathiocyanodiamminochromate(III) monohydrate

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

chlorpromazinium reineckate

chlorpromazinium reineckate

Conditions
ConditionsYield
In water E-2 M solns. were mixed; ppt. was filtered, thoroughly washed with distd. water, dried at room temp., elem. anal.;99.5%
sodium hexanitro cobaltate(III)

sodium hexanitro cobaltate(III)

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

chlorpromazinium cobaltnitrite

chlorpromazinium cobaltnitrite

Conditions
ConditionsYield
In water E-2 M solns. were mixed; ppt. was filtered, thoroughly washed with distd. water, dried at room temp., elem. anal.;99.5%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

methyl iodide
74-88-4

methyl iodide

SKF 2680J
362-02-7

SKF 2680J

Conditions
ConditionsYield
Stage #1: chlorpromazine hydrochloride With sodium hydroxide In diethyl ether
Stage #2: methyl iodide In acetonitrile Reflux; Darkness;		99%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

chloropromazine radical cation

chloropromazine radical cation

Conditions
ConditionsYield
With potassium thioacyanate In water Rate constant; Ambient temperature; with different oxidizing agents, salt concentration, and various pH range;97%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

2-chloro-10-(3-dimethylaminopropyl)phenothiazine 5-oxide hydrochloride
316-07-4

2-chloro-10-(3-dimethylaminopropyl)phenothiazine 5-oxide hydrochloride

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol a) RT, overnight, b) reflux, 2 h;95.5%
With hydrogenchloride; potassium metaperiodate In water Ambient temperature;
With n-C4F9; perfluoro-cis-2,3-dialkyloxaziridine; n-C3F7 In various solvent(s) at -40℃; for 0.5h; Yield given;
ethyl bromide
74-96-4

ethyl bromide

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

3-(2-chloro-10H-phenothiazin-10-yl)-N-ethyl-N,N-dimethylpropan-1-aminium bromide
153871-17-1

3-(2-chloro-10H-phenothiazin-10-yl)-N-ethyl-N,N-dimethylpropan-1-aminium bromide

Conditions
ConditionsYield
Stage #1: chlorpromazine hydrochloride With sodium hydroxide In diethyl ether
Stage #2: ethyl bromide In acetonitrile Reflux; Darkness;		93%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

zinc(II) chloride
7646-85-7

zinc(II) chloride

Zn(C6H4SN((CH2)3NH(CH3)2)C6H3Cl)4Cl2(4+)*4Cl(1-)=[Zn(C6H4SN((CH2)3NH(CH3)2)C6H3Cl)4Cl2]Cl4

Zn(C6H4SN((CH2)3NH(CH3)2)C6H3Cl)4Cl2(4+)*4Cl(1-)=[Zn(C6H4SN((CH2)3NH(CH3)2)C6H3Cl)4Cl2]Cl4

Conditions
ConditionsYield
In water slow addn. of soln. of ZnCl2 to soln. of ligand with stirring, stirring (room temp., 3 h), conctg., cooling; decanting viscous liq., redissolving in methanol with stirring at 60°C, suction filtn., washing (2-3 times, cold methanol), drying (air),drying (vac.), recrystn. (hot methanol), elem. anal.;92.5%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

bis(trifluoromethane)sulfonimide lithium
90076-65-6

bis(trifluoromethane)sulfonimide lithium

C2HF6NO4S2*C17H19ClN2S
1309962-25-1

C2HF6NO4S2*C17H19ClN2S

Conditions
ConditionsYield
With water at 20℃; for 2h;91%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

2-deuterio-10-[3-(dimethylamino)-1-propyl]phenothiazine

2-deuterio-10-[3-(dimethylamino)-1-propyl]phenothiazine

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); 1-deuteriodiphenylmethanol; 3-(2,6-dibenzhydryl-4-methylphenyl)-4,5-dimethyl-1-(2,4,6-trimethylbenzyl)imidazolium chloride; caesium carbonate In toluene at 90℃; for 16h; Inert atmosphere;90%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

potassium vinyltrifluoroborate

potassium vinyltrifluoroborate

N,N-dimethyl-3-(2-vinyl-10H-phenothiazin-10-yl)propan-1-amine

N,N-dimethyl-3-(2-vinyl-10H-phenothiazin-10-yl)propan-1-amine

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 90℃; for 2h; Schlenk technique; Inert atmosphere;81%
hexaammonium heptamolybdate tetrahydrate

hexaammonium heptamolybdate tetrahydrate

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

Mo2O4(C6H4SN(CH2)3N(CH3)2C6H3Cl)2(H2O)2

Mo2O4(C6H4SN(CH2)3N(CH3)2C6H3Cl)2(H2O)2

Conditions
ConditionsYield
In hydrogenchloride (NH4)6Mo7O24*4H2O in 2 M HCl was added to soln. of ligand in water with vigorous stirring, suspn. set aside for 2 h; suspn. filtered, washed with water, ethanol and dried in vacuo over fused CaCl2; elem. anal.;76%
yttrium(III) nitrate
13494-98-9

yttrium(III) nitrate

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

Y(3+)*2C17H19N2SCl*3NO3(1-) = [Y(C17H19N2SCl)2(NO3)2](NO3)

Y(3+)*2C17H19N2SCl*3NO3(1-) = [Y(C17H19N2SCl)2(NO3)2](NO3)

Conditions
ConditionsYield
In water warming (60°C, 30 min); washing (water, Et2O), drying (vac.); elem. anal.;70%
potassium hexachloropalatinate(IV)

potassium hexachloropalatinate(IV)

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

chlorpromazine chlorpromazinehydrochloridepentachloridoplatinate(IV)

chlorpromazine chlorpromazinehydrochloridepentachloridoplatinate(IV)

Conditions
ConditionsYield
In water at 20℃; Darkness;65.69%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

promazine
58-40-2

promazine

Conditions
ConditionsYield
In water Irradiation; in micelles with detergent Brij 58 in presence of 2,5-dimethylfurane;56%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

uranyl(VI) acetate dihydrate

uranyl(VI) acetate dihydrate

UO2(CH3COO)2(C6H4SN(CH2CH2CH2N(CH3)2)C6H3Cl)(H2O)2

UO2(CH3COO)2(C6H4SN(CH2CH2CH2N(CH3)2)C6H3Cl)(H2O)2

Conditions
ConditionsYield
In water soln. refluxed for 6 h; cooling under ice-cold water for 4 d; ppt. filtered and dried in vac.; elem. anal.;50%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

A

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

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

B

promazine
58-40-2

promazine

Conditions
ConditionsYield
In water Irradiation;A 5%
B 38%
In water Product distribution; Irradiation; in micelles with several detergents, different atmospheres and reaction times;A 5%
B 38%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

palladium dichloride

palladium dichloride

Pd(C6H4SN(CH2CH2CH2NH(CH3)2)C6H3Cl)Cl3
75234-56-9, 82489-75-6

Pd(C6H4SN(CH2CH2CH2NH(CH3)2)C6H3Cl)Cl3

Conditions
ConditionsYield
In hydrogenchloride; water stirring (ambient temp., 1 h); pptn. on cooling (4°C), washing (water, MeOH), drying (vac.), recrystn. (MeOH); elem. anal.;37.8%
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

urea
57-13-6

urea

10-(3-(dimethylamino)propyl)-10H-phenothiazine-2-carbonitrile
7678-64-0

10-(3-(dimethylamino)propyl)-10H-phenothiazine-2-carbonitrile

Conditions
ConditionsYield
With nickel(II) acetylacetonate; potassium fluoride; phenylsilane; zinc; bis(2-diphenylphosphinoethyl)phenylphosphine In 1-methyl-pyrrolidin-2-one at 90 - 140℃; for 20h;37%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

N,N'-bis-[3-(2-chloro-phenothiazin-10-yl)-propyl]-N,N,N',N'-tetramethyl-N,N'-butanediyl-di-ammonium; dibromide

N,N'-bis-[3-(2-chloro-phenothiazin-10-yl)-propyl]-N,N,N',N'-tetramethyl-N,N'-butanediyl-di-ammonium; dibromide

Conditions
ConditionsYield
With ethanol
8-Anilino-1-naphthalenesulfonic acid
82-76-8

8-Anilino-1-naphthalenesulfonic acid

chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-amine; mono-(8-anilino-naphthalene-1-sulfonate)
71643-78-2

[3-(2-chloro-phenothiazin-10-yl)-propyl]-dimethyl-amine; mono-(8-anilino-naphthalene-1-sulfonate)

Conditions
ConditionsYield
In water
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

C17H20ClN2S

C17H20ClN2S

Conditions
ConditionsYield
With potassium metaperiodate; phosphoric acid; sulfuric acid In water
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

glycerol
56-81-5

glycerol

promazine Hydrochloride
53-60-1

promazine Hydrochloride

Conditions
ConditionsYield
other matrices, also with 4-chlorophenylalanine ethylester, time of irradiation, analyte concentration, matrix selection and matrix additives, primary beam density on the beam-induced dehalogenation in liquid secondary ion mass spectroscopy;
chlorpromazine hydrochloride
69-09-0

chlorpromazine hydrochloride

methyl iodide
74-88-4

methyl iodide

methochlorpromazine iodide

methochlorpromazine iodide

Conditions
ConditionsYield
With sodium hydroxide 1) water; 2) acetone, 25 deg C, 1 h;

Chlorpromazine hydrochloride Consensus Reports

Reported in EPA TSCA Inventory.

Chlorpromazine hydrochloride Specification

The IUPAC name of Chloropromazine hydrochloride is 3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine hydrochloride. With the CAS registry number 69-09-0, it is also named as 10-(3-Dimethylaminopropyl)-2-chlorophenothiazine monohydrochloride; Aminazin monohydrochloride; Fenactil monohydrochloride; Lomazine; Megaphen hydrochloride; Plegomazin; Tranzine; Phenothiazine, 2-chloro-10-(3-(dimethylamino)propyl)-, monohydrochloride. This product belongs to intermediates & fine chemicals and pharmaceuticals.

The Chloropromazine hydrochloride is white or creamy-white odorless crystalline powder with very bitter taste. It can be used as an Antiemetic and Antipsychotic. And it may decompose on exposure to air and light. In addition, it is incompatible in aqueous solution with sodium salts of barbiturates and other alkaline solutions. Solutions may be stabilized by addition of antioxidants and storing under nitrogen.

This chemical is toxic if swallowed and inhalation. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.20; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.17; (4)ACD/LogD (pH 7.4): 3.26; (5)ACD/BCF (pH 5.5): 4.93; (6)ACD/BCF (pH 7.4): 60.69; (7)ACD/KOC (pH 5.5): 15; (8)ACD/KOC (pH 7.4): 184.58; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Enthalpy of Vaporization: 70.89 kJ/mol; (13)Vapour Pressure: 2.72E-08 mmHg at 25°C; (14)Rotatable Bond Count: 4; (15)Exact Mass: 354.072425; (16)MonoIsotopic Mass: 354.072425; (17)Topological Polar Surface Area: 31.8; (18)Heavy Atom Count: 22 ; (19)Complexity: 339.

People can use the following data to convert to the molecule structure. SMILES: Cl.Clc2cc1N(c3c(Sc1cc2)cccc3)CCCN(C)C; InChI: InChI=1/C17H19ClN2S.ClH/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20;/h3-4,6-9,12H,5,10-11H2,1-2H3;1H.

The following is the toxicity data which has been tested. 
 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intraperitoneal 160mg/kg (160mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 558, 1960.
chicken LD50 intravenous 28mg/kg (28mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 558, 1960.
guinea pig LD50 intraperitoneal 109mg/kg (109mg/kg)   Pharmazie. Vol. 38, Pg. 749, 1983.
guinea pig LD50 subcutaneous 420mg/kg (420mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
man TDLo intravenous 1786ug/kg/2D- (1.786mg/kg) BEHAVIORAL: IRRITABILITY

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER		 Biological Psychiatry. Vol. 18, Pg. 1441, 1983.
 
man TDLo oral 6071ug/kg (6.071mg/kg)   Israel Journal of Medical Sciences. Vol. 5, Pg. 1254, 1969.
man TDLo oral 18mg/kg (18mg/kg)   Israel Journal of Medical Sciences. Vol. 5, Pg. 1254, 1969.
monkey LDLo oral > 30mg/kg (30mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY

BEHAVIORAL: MUSCLE WEAKNESS		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 122, Pg. 129, 1959.
 
mouse LC50 inhalation 40mg/m3/2H (40mg/m3)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1106, 1986.
mouse LD50 intraperitoneal 92200ug/kg (92.2mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 558, 1960.
mouse LD50 intravenous 20mg/kg (20mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 808, 1971.
mouse LD50 oral 135mg/kg (135mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERATION OF CLASSICAL CONDITIONING		 Chemical and Pharmaceutical Bulletin. Vol. 24, Pg. 1179, 1976.
 
mouse LD50 subcutaneous 420mg/kg (420mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 22, Pg. 301, 1964.
rabbit LD50 intravenous 5mg/kg (5mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 15, 1972.
rat LC50 inhalation 40mg/m3/2H (40mg/m3)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1106, 1986.
rat LD50 intraperitoneal 62mg/kg (62mg/kg)   Psychopharmacologia Vol. 12, Pg. 142, 1968.
rat LD50 intravenous 25mg/kg (25mg/kg)   Fortschritte der Arzneimittelforschung. Progress in Drug Research. Vol. 5, Pg. 269, 1963.
rat LD50 oral 145mg/kg (145mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 148, Pg. 151, 1965.
rat LD50 unreported 90mg/kg (90mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 15, 1972.
women TDLo intravenous 822ug/kg (0.822mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP		 Annals of Emergency Medicine. Vol. 17, Pg. 380, 1988.
 
women TDLo oral 6mg/kg (6mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: OTHER CHANGES		 Postgraduate Medical Journal. Vol. 60, Pg. 564, 1984.
 
women TDLo oral 35gm/kg/16Y-I (35000mg/kg) BEHAVIORAL: REGIDITY

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Biological Psychiatry. Vol. 18, Pg. 1441, 1983.
 

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