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Chlorpromazine hydrochloride

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Name

Chlorpromazine hydrochloride

EINECS 200-701-3
CAS No. 69-09-0 Density 1.077 g/cm3 (15 C)
PSA 31.78000 LogP 5.76140
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;

Article Data 3

Chlorpromazine hydrochloride Synthetic route

92-39-7

2-chlorophenothiazine

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

69-09-0

chlorpromazine hydrochloride

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 at 80℃; for 1h;85%

oxovanadium(IV) sulfate

50-53-3

chloropromazine cation radical

A

69-09-0

chlorpromazine hydrochloride

B

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;
69-09-0

chlorpromazine hydrochloride

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
69-09-0

chlorpromazine hydrochloride

potassium hexacyanoferrate(III)

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%

ammonium tetrathiocyanodiamminochromate(III) monohydrate

69-09-0

chlorpromazine hydrochloride

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)

69-09-0

chlorpromazine hydrochloride

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%
69-09-0

chlorpromazine hydrochloride

74-88-4

methyl iodide

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%
69-09-0

chlorpromazine hydrochloride

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%
69-09-0

chlorpromazine 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;
74-96-4

ethyl bromide

69-09-0

chlorpromazine hydrochloride

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 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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