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50-53-3

50-53-3 Structure

50-53-3 Structure
IdentificationBack Directory
[Name]

Chlorpromazine
[CAS]

50-53-3
[Synonyms]

2601-A
Esmind
Prazil
Prozin
Elmarin
Hibanil
HL 5746
Hibernal
Fenactil
Fenaktyl
Chlor-PZ
Contomin
Aminazin
SKF-2601
Torazina
Phenactyl
Phenathyl
Thorazine
Aminazine
4560 R.P.
Aminasine
Amplictil
Largactyl
Novomazina
Ampliactil
Amplicitil
Psychozine
SKF 2601-A
Thiazenone
Plegomasine
Propaphenin
Cromedazine
Fraction AB
Chlorderazin
Chlorpromados
Clorpromazina
Chlorpromazin
Chlor-Promanyl
Chlorpromazine
Prazilpromactil
Chloropromazine
2-Chloropromazine
Largactilothiazine
CHLORPROMAZINE,USP
CHLORPROMAZINE(ALKALI)
2-Cloro-10 (3-dimetilaminopropil)fenotiazina
Chlorpromazine (base and/or unspecified salts)
Chloro-2-dimethylamino-3 propyl-10 phenothiazine
2-Chloro-10-[3-(dimethyamino)propyl]phenothiazine
3-(2-chlorophenothiazin-10-yl)propyldimethylamine
Phenothiazine, 2-chloro-10-[3-(dimethylamino)propyl]-
10H-Phenothiazine-10-propanamine, 2-chloro-N,N-dimethyl-
3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine
3-(2-chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine
3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine
[EINECS(EC#)]

200-045-8
[Molecular Formula]

C17H19ClN2S
[MDL Number]

MFCD00133295
[MOL File]

50-53-3.mol
[Molecular Weight]

318.864
Chemical PropertiesBack Directory
[Appearance]

Oily liquid; amine odor.
[Melting point ]

56.5°C
[Boiling point ]

bp0.8 200-205°
[density ]

1.1644 (rough estimate)
[refractive index ]

1.6230 (estimate)
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

pKa 9.3(H2O,t =24±1) (Uncertain)
[color ]

White to Off-White
[Henry's Law Constant]

6.5×104 mol/(m3Pa) at 25℃, Ebert et al. (2023)
[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.
[NIST Chemistry Reference]

Chlorpromazine(50-53-3)
[EPA Substance Registry System]

10H-Phenothiazine10-propanamine, 2-chloro-N,N-dimethyl-(50-53-3)
Hazard InformationBack Directory
[Uses]

antiemetic, antipsychotic
[Definition]

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

Toxic by ingestion.
[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.
[Brand name]

Thorazine (GlaxoSmithKline).
[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.
[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.
[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.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[REACH Registrations]

Active
[Hazardous Substances Data]

50-53-3(Hazardous Substances Data)
[Toxicity]

LD50 oral in rat: 142mg/kg
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