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Chlorpromazine

CAS：50-53-3
MW:318.86416
MF：C17H19ClN2S

This phenothiazine with sedative properties is used inhuman medicines and has induced contact dermatitisin nurses or in those working in the pharmaceuticalindustry. It is also used in veterinary medicine to avoidmortality of pigs during transportation. It is a sensitizerand a photosensitizer. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Chlorpromazine

1.2 Synonyms: [3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-amine; 10-(3-Dimethylaminopropyl)-2-chlorophenothiazine; 10H-Phenothiazine-10-propanamine, 2-chloro-N,N-dimethyl-; 2601-A; 2-chloro-10-(3-(dimethylamino)propyl)-phenothiazine; 2-Chloro-10-(3-dimethylaminopropyl)phenothiazine; 2-Chloro-10-[3-(dimethylamino)propyl]phenothiazine; 3-(2-chloro-10H-phénothiazin-10-yl)-N,N-diméthylpropan-1-amine; 3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine; 3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine; 3-(2-chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine; 4560 R.P.; Aminazin; chloropromazine; Chlorpromazine (base and/or unspecified salts); CHLORPROMAZINE(ALKALI); chlorpromazinum; Chlor-PZ; Contomin; CPZ; CPZ (VAN); EINECS 200-045-8; Elmarin; Esmind; Hibanil; HL 5746; Phenothiazine, 2-chloro-10-[3- (dimethylamino)propyl]-; Phenothiazine, 2-chloro-10-[3-(dimethylamino)propyl]-; Prazil; Prozin;

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1.3 CAS No.: 50-53-3

1.4 CID: 2726

1.5 EINECS: 200-045-8

1.6 Molecular Formula: C17H19ClN2S

1.7 Inchi: InChI=1S/C17H19ClN2S/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

1.8 InChkey: ZPEIMTDSQAKGNT-UHFFFAOYSA-N

1.9 Canonical Smiles: CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)Cl

1.10 Isomers Smiles: CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)Cl

2. Properties

2.1 Appearance: Solid

2.2 Chemical Properties: Oily liquid; amine odor.

2.3 Color/Form: Oily liquid
White, crystalline solid

2.4 Contact Allergens: This phenothiazine with sedative properties is used inhuman medicine and induced contact dermatitis in nursesor those working in the pharmaceutical industry. It is alsoused in veterinary medicine to avoid mortality of pigs duringtransportation. It is a sensitizer and a photosensitizer.

2.5 Decomposition: When heated to decomposition it emits very toxic fumes of /hydrogen chloride/, nitroxides, and sulfoxides.

2.6 Odor: Amine odor

2.7 PH: Alkaline reaction

2.8 pKa: pKa 9.3(H2O,t =24±1) (Uncertain)

2.9 Water Solubility: 4.17e-03 g/L

2.10 Spectral Properties: MAX ABSORPTION: 250 NM (LOG E= 4.5); 320 NM (LOG E= 3.5)
IR: 5200 (Coblentz Society Spectral Collection)
MASS: 235 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
Intense mass spectral peaks: 58 m/z, 86 m/z, 232 m/z, 272 m/z, 318 m/z

2.11 Stability: Oral preparations of chlorpromazine hydrochloride should be stored in tightly closed containers Slight yellowish discoloration of the oral solutions or injection will not affect potency or efficacy, but they should not be used if markedly discolored or if a precipitate is present. At the time of manufacture, air in the containers of the commercially available chlorpromazine hydrochloride injection is replaced with nitrogen to avoid oxidation.

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3. Use and Manufacturing

3.1 Definition: ChEBI: A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.

3.2 Description: Chlorpromazine (CAS 50-53-3) is a phenothiazine derivative that is commonly used as an antipsychotic medication. It is a white to pale yellow crystalline powder with a slight odor. The chemical structure of chlorpromazine consists of a tricyclic ring system with a side chain containing a chlorine atom. It is sparingly soluble in water, but soluble in alcohol and chloroform.

Applicable Fields
Psychiatry: Chlorpromazine is primarily used in the field of psychiatry to treat various mental disorders, including schizophrenia, bipolar disorder, and severe behavioral problems. Its mechanism of action involves blocking the effects of dopamine and other neurotransmitters in the brain, which helps to alleviate symptoms such as hallucinations, delusions, and agitation.

Storage Conditions
Store in a cool, dry place.

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3.3 Usage: In psychiatric practice, chlorpromazine is used in various conditions of psychomotorexcitement in patients with schizophrenia, chronic paranoid and also manic-depressiveconditions, neurosis, alcohol psychosis and neurosis accompanied by excitement, fear,stress, and insomnia. In comparison with other neuroleptics, chlorpromazine is unique inthat it has an expressed sedative effect. It is sometimes used in anesthesiological practicefor potentiating narcosis. It also has moderate anticonvulsant action.

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4. Safety and Handling

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

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4.2 Octanol/Water Partition Coefficient: log Kow= 5.35

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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4.4 Formulations/Preparations: Rectal suppositories 25 or 100 mg
Oral capsules, extended release 30, 75, 150, 200, & 300 mg; Solution 10 mg/5 ml; Solution, concentrate 30 mg/ml & 100 mg/ml.

4.5 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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4.6 Toxicity: LD50 oral in rat: 142mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 3

Reproductive toxicity, Additional category for effects on or via lactation

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H317 May cause an allergic skin reaction H331 Toxic if inhaled H362 May cause harm to breast-fed children H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P271 Use only outdoors or in a well-ventilated area. P201 Obtain special instructions before use. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P263 Avoid contact during pregnancy and while nursing. P273 Avoid release to the environment.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P311 Call a POISON CENTER/doctor/\u2026 P308+P313 IF exposed or concerned: Get medical advice/ attention. P391 Collect spillage.
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

50-53-3Total: 24 Synthesis Route

69-09-0 235 Suppliers

50-53-3 50 Suppliers

92-39-7 141 Suppliers

50-53-3 50 Suppliers

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7. Precursor and Product

precursor:

109-54-6

41951-57-9

50-53-3

69-09-0

92-39-7

76637-14-4

4414-83-9

101-17-7

969-99-3

3953-65-9

product:

1225-64-5

5690-75-5

50-53-3

2095-62-7

50673-96-6

58-40-2

3926-66-7

969-99-3

3926-64-5

3930-47-0

3953-65-9

8. Computed Properties

Molecular Weight：318.86416g/mol
Molecular Formula：C₁₇H₁₉ClN₂S
Compound Is Canonicalized：True
XLogP3-AA：318.0957475
Monoisotopic Mass：318.0957475
Complexity：339
Rotatable Bond Count：4
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：31.8
Heavy Atom Count：：21
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADceB7AABEAAAAAAAAAAAAAAAAAAAAAAA8YIAAAAAAAACxQAAAHAYAAAAACArBUCQywYMAAAiAACRCQACCAAAhDxAIiBwIZogIIGLh05GEIAhggADoyAcQAAAAAAIAAAIAAQAABAAABAACAAAAAAAAAA==

9.Other Information

Description: This phenothiazine with sedative properties is used in human medicines and has induced contact dermatitis in nurses or in those working in the pharmaceutical industry. It is also used in veterinary medicine to avoid mortality of pigs during transportation. It is a sensitizer and a photosensitizer.

Chemical Properties: Oily liquid; amine odor.

Uses: In psychiatric practice, chlorpromazine is used in various conditions of psychomotor excitement in patients with schizophrenia, chronic paranoid and also manic-depressive conditions, neurosis, alcohol psychosis and neurosis accompanied by excitement, fear, stress, and insomnia. In comparison with other neuroleptics, chlorpromazine is unique in that it has an expressed sedative effect. It is sometimes used in anesthesiological practice for potentiating narcosis. It also has moderate anticonvulsant action.

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Uses: antiemetic, antipsychotic

Uses: Chlorpromazine is approved by FDA for use in humans for the management of psychotic disorders (i.e., control of mania, treatment of schizophrenia); control of nausea and vomiting; relief of apprehension before surgery; acute intermittent porphyria; adjunctive treatment of tetanus; intractable hiccups; combativeness or explosive hyperexcitable behavior in children aged 1–12 years; and short-term treatment of hyperactivity in children with symptoms of impulsivity, difficulty sustaining attention, aggressiveness, mood lability, and poor frustration tolerance. Chlorpromazine is commonly used off-label for treatment of behavioral symptoms associated with dementia in the elderly and psychosis and agitation related to Alzheimer’s dementia; however, it carries a boxed warning regarding increased risk of death in patients with dementia-related psychosis. Chlorpromazine is also used off-label for managing agitation in terminal cancer patients, autonomic dysreflexia, cancer pain, adjunctive treatment of cholera, migraine headaches, opioid withdrawal, ocular pain, paralytic ileus, and phantom limb syndrome.
In veterinary medicine, the use of chlorpromazine has been largely replaced by the phenothiazine acepromazine due to its more favorable pharmacokinetic profile. Chlorpromazine may be used as an antiemetic for small animals or for preoperative sedation. Chlorpromazine may also be used for management of hypertension in dogs and cats.

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Definition: ChEBI: A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.

Brand name: Thorazine (GlaxoSmithKline).

Hazard: Toxic by ingestion.

Contact allergens: This phenothiazine with sedative properties is used in human medicine and induced contact dermatitis in nurses or those working in the pharmaceutical industry. It is also used in veterinary medicine to avoid mortality of pigs during transportation. It is a sensitizer and a photosensitizer.

Chemical Synthesis: Chlorpromazine, 2-chloro-10-(3-dimethylaminopropyl)phenothiazine, is synthesized in an analogous manner, except by alkylation of 2-chlorophenothiazine with 3-dimethylaminopropylchloride.

Environmental Fate: Acute and chronic toxicity due to chlorpromazine generally manifests as an extension of normal pharmacological activity. The precise mechanism of action of chlorpromazine, and other phenothiazines, is unknown; however, it is thought to primarily involve antagonism of dopaminergic (D2) neurotransmission at synaptic sites and blockade of postsynaptic dopamine receptor sites at the subcortical levels of the reticular formation, limbic system, and hypothalamus. This activity contributes to chlorpromazine’s extrapyramidal reactions. Chlorpromazine also has strong central and peripheral activity directed against adrenergic receptors and weak activity against serotonergic, histaminic (H1), and muscarinic receptors. Chlorpromazine has slight ganglionic blocking action. Chlorpromazine is known to depress vasomotor reflexes medicated by the hypothalamus and/or brain stem; inhibit release of growth hormone; antagonize secretion of prolactin release-inhibiting hormone; and reduce secretion of corticotropin-regulatory hormone.
Chlorpromazine also has direct effects on cardiac myocytes; it can induce early after-depolarizations, block depolarizing sodium channels, and cause significant prolongation of the QTc interval.
Chlorpromazine may be irritating to eyes, mucous membranes, and skin. Contact and inhalation should be avoided.

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Metabolic pathway: The in vivo photodegradation of chlorpromazine in rat skin exposed to UV-A results in the formation of promazine and 2-hydroxypromazine in irradiated rats, but not in the skin of rats kept in the dark. Chlorpromazine sulfoxide is a major metabolite of chlorpromazine, found in smaller quantity in the skin of irradiated rats compared with those kept in the dark. Chlorpromazine sulfoxide is not a photoproduct of chlorpromazine under the experimental conditions.

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Toxicity evaluation: Chlorpromazine exists as both a vapor and particulate at ambient atmospheric conditions. Chlorpromazine vapor is degraded by photochemically produced hydroxyl radicals with an estimated half-life of 1.6 h. Chlorpromazine particulate is removed by wet or dry deposition. Chlorpromazine is likely to be immobile in soil (Koc 9900, pKa 9.3) and to adsorb to sediment if released into water. It is not expected to volatilize from soil or water. There is high potential for bioconcentration.

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10. Toltal 41 Suppliers View more

Hangzhou Dingyan Chem Co.,Ltd

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Amitychem Corporation

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Factory supply chlorpromazine Cas 50-53-3 from China

Hebei Crovell Biotech Co. Ltd

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Prochlorperazine CAS:50-53-3 99% Higher Quality

Fuao Chemical Technology Co., Ltd.

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Wuhan Circle Star Chem-medical Technology Co.,Ltd

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11. Related Questions

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12. Realated Product Infomation