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Chlorpromazine hydrochloride

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Chlorpromazine hydrochloride Basic information
Chlorpromazine hydrochloride Chemical Properties
  • Melting point:192-196°C
  • Density 1.2221 (estimate)
  • Flash point:9℃
  • storage temp. 2-8°C
  • solubility Very soluble in water, freely soluble in ethanol (96 per cent). It decomposes on exposure to air and light.
  • form Powder/Solution
  • color White to off-white or clear colorless
  • PHpH (50g/L, 25℃) : 4.0~5.0
  • Water Solubility >=10 g/100 mL at 24 ºC
  • Merck 14,2185
  • BRN 3779989
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sesnsitive.
  • CAS DataBase Reference69-09-0(CAS DataBase Reference)
  • EPA Substance Registry SystemChlorpromazine hydrochloride (69-09-0)
Safety Information
  • Hazard Codes T+,T,F
  • Risk Statements 25-26-39/23/24/25-23/24/25-11
  • Safety Statements 28-36/37-45-16
  • RIDADR UN 2811 6.1/PG 1
  • WGK Germany 3
  • RTECS SO1750000
  • 3-10-21
  • TSCA Yes
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 29173980
  • ToxicityLD50 orally in rats: 225 mg/kg (Goldenthal)
MSDS
Chlorpromazine hydrochloride Usage And Synthesis
  • Chemical PropertiesCrystalline Solid
  • OriginatorThorazine, SKF, US ,1954
  • UsesUsed as an Antiemetic, Antipsychotic
  • UsesChlorpromazine hydrochloride is used in the treatment of schizophrenia; anti-emetic; as an antipsychotic in pills, injections, and suppositories; to relieve nausea and vomiting associated with malignant diseases. In veterinary medicine, it is used as an anti-emetic, tranquilizer and sedative. It has slight antihistaminic and anti adrenaline actions. It is a peripheral vasodilator and adepressant that blocks dopamine receptors in the central nervous system.
  • UsesAntiemetic;Dopamine antagonist
  • DefinitionChEBI: The hydrochloride salt of chlorpromazine.
  • Manufacturing ProcessTo a boiling suspension of 11.6 g of chlorophenothiazine (consisting of a mixture of two isomers melting at 196° to 198°C and 116° to 117°C, respectively, the latter in minor proportion) and 2.4 g of sodium amide (80%) in 60 cc of xylene, there are added over a period of one hour 7.5 g of 3-
    dimethylamino-1-chloropropane in solution in its own weight of xylene. At the end of the addition, heating is continued for one hour under reflux. After cooling, the contents are taken up in acidified water and the xylene separated. The aqueous layer is made strongly alkaline by means of sodium hydroxide in order to liberate the base and this is extracted with ether. On distillation of the ethereal extract there is obtained 10-(3'-dimethylamino-propyl)- chlorophenothiazine which distills at 200° to 205°C under a pressure of 0.8 mm Hg. Its hydrochloride, recrystallized from chlorobenzene, melts at 177° to 178°C. The chlorophenothiazine may be prepared by reacting mchlorodiphenylamine with sulfur in the presence of an iodine catalyst.
  • brand nameThorazine (GlaxoSmithKline).
  • Therapeutic FunctionTranquilizer
  • General DescriptionChlorpromazinehydrochloride, 2-chloro-10-[3-(dimethylamino)propyl]phenothiazine monohydrochloride (Thorazine), was the first phenothiazinecompound introduced into therapy. It is still usefulas an antipsychotic. Other uses are in nausea, vomiting, andhiccough. Oral doses of chlorpromazine and thioridazinehave systemic availability of 25% to 35% because of significantfirst-pass metabolism. Chlorpromazine and other phenothiazinesare metabolized extensively by CYP2D6. In contrast, bioavailability of chlorpromazine may beincreased up to 10-fold with injections, but the clinical doseusually is decreased by only threefold to fourfold.Chlorpromazine may weakly induce its own hepatic metabolism,because its concentration in blood is lower after severalweeks of treatment at the same dosage. Alterations of GImotility also may contribute. The drug has significant sedativeand hypotensive properties, possibly reflecting centralhistaminergic and peripheral α1-noradrenergic blockingactivity, respectively. Effects of peripheral anticholinergic activityare common. As with the other phenothiazines, the effectsof other CNS-depressant drugs, such as sedatives andanesthetics, can be potentiated.
  • General DescriptionWhite or creamy-white odorless crystalline powder with very bitter taste. pH (5% aqueous solution) 4.0-5.5. pH (10% aqueous solution) 4-5.
  • Air & Water ReactionsDecomposes on exposure to air and light. becoming yellow, pink and, finally, violet. Water soluble.
  • Reactivity ProfileChlorpromazine hydrochloride 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.
  • Fire HazardFlash point data for Chlorpromazine hydrochloride are not available; however, Chlorpromazine hydrochloride is probably combustible.
  • Safety ProfilePoison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. An experimentalteratogen. Experimental reproductive effects. An anti-emetic and antipsychotic drug. Human systemic effects: anorexia (human), excitement, gastrointestinal changes, irritability, pulse rate increase, respiratory stimulation, rigidity, somnolence, sweating. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and SOx.
  • Veterinary Drugs and TreatmentsThe clinical use of chlorpromazine as a neuroleptic agent has diminished, but the drug is still used for its antiemetic effects in small animals and occasionally as a preoperative medication and tranquilizer. As an antiemetic, chlorpromazine will inhibit apomorphineinduced emesis in the dog but not the cat. It will also inhibit the emetic effects of morphine in the dog. It does not inhibit emesis caused by copper sulfate, or digitalis glycosides.
    Once the principle phenothiazine used in veterinary medicine, chlorpromazine has been largely supplanted by acepromazine. It has similar pharmacologic activities as acepromazine, but is less potent and has a longer duration of action. For further information, refer to the acepromazine monograph.
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