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52-86-8

52-86-8 Structure

52-86-8 Structure
IdentificationMore
[Name]

Haloperidol
[CAS]

52-86-8
[Synonyms]

4-[4-(4-CHLOROPHENYL)-4-HYDROXY-1-PIPERIDINYL]-1-(4-FLUOROPHENYL)-1-BUTANONE
4-[4-(4-CHLOROPHENYL)-4-HYDROXYPIPERIDINO]-4'-FLUOROBUTYROPHENONE
AKOS 91337
HALOPERIDOL
1-(3-p-Fluorobenzoylpropyl)-4-p-chlorophenyl-4-hydroxypiperidine
1-Butanone, 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-
1-butanone,4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)
4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanon
4-(4-(para-Chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone
4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4’-fluoro-butyrophenon
4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4’-fluorobutyrophenone
4-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone
4-(4-hydroxy-4’-chloro-4-phenylpiperidino)-4’-fluorbutyrophenone
4-(4-hydroxy-4’-chloro-4-phenylpiperidino)-4’-fluorobutyrophenone
4-(4-Hydroxy-4'-chloro-4-phenylpiperidino)-4'-fluorobutyrophenone
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-4’-(4-flurophenyl)-1-butanone
4’-fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-butyrophenon
4’-fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)butyrophenone
4’-fluoro-4-(4-hydroxy-4-(4’-chlorophenyl)piperidino)butyrophenone
4’-fluoro-4-(4-hydroxy-4-p-chlorophenylpiperidino)butyrophenone
[EINECS(EC#)]

200-155-6
[Molecular Formula]

C21H23ClFNO2
[MDL Number]

MFCD00051423
[Molecular Weight]

375.86
[MOL File]

52-86-8.mol
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Powder
[Melting point ]

152 °C
[mp ]

152 °C
[Boiling point ]

529.0±50.0 °C(Predicted)
[density ]

1.1820 (estimate)
[Fp ]

9℃
[storage temp. ]

2-8°C
[solubility ]

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.39 mg/mL
[pka]

8.3(at 25℃)
[form ]

powder
[color ]

white
[Water Solubility ]

2.058mg/L(22.5 ºC)
[Usage]

Antidyskinetic; antipsychotic
[Merck ]

4598
[CAS DataBase Reference]

52-86-8(CAS DataBase Reference)
[NIST Chemistry Reference]

Haloperidol(52-86-8)
[EPA Substance Registry System]

52-86-8(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

R60:May impair fertility.
R61:May cause harm to the unborn child.
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
[Safety Statements ]

S53:Avoid exposure-obtain special instruction before use .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

EU1575000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

2933399090
[Hazardous Substances Data]

52-86-8(Hazardous Substances Data)
[Toxicity]

LD50 orally in rats: 165 mg/kg (Goldenthal); i.p. in mice: 60 mg/kg (Collins, Horlington)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Thionyl chloride-->Gamma Butyrolactone-->Fluorobenzene-->Butyrophenone-->Ammonia-->4-(4-chlorophenyl)piperidin-4-ol hydrochloride-->Hydrochloric acid
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone(52-86-8).msds
Hazard InformationBack Directory
[Chemical Properties]

White Crystalline Powder
[Originator]

Haldol,Janssen-Le Brun,France,1960
[Uses]

Haloperidol is one of the most actively used modern neuroleptics. Its high antipsychotic activity is combined with a moderate sedative effect. It effectively stops various types of psychomotor excitement. It is used for schizophrenic psychoses, manic, paranoid, and delirious conditions, depression, psychomotor excitement of various origins, and for delirium and hallucinations of different origin.
[Uses]

Antidyskinetic; antipsychotic
[Definition]

ChEBI: A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.
[Manufacturing Process]

A stirred slurry of 120.0 parts 4-(4-chlorophenyl)-piperidin-4-ol hydrochloride and 40.0 parts of potassium iodide in 500 parts of water is warmed to a temperature of about 35°C under a nitrogen atmosphere. Then, 70.0 parts of potassium hydroxide is added. After further heating to about 55°C. 138.0 parts of 1,1 dimethoxy-1-(4-fluorophenyl)-4-chlorobutane is added. The temperature is then raised to about 102°C and heating continued for 3.5 hours. After cooling to about 75°C. 785 parts of toluene is added to the reaction mixture and stirred for about 5 minutes. An additional 320 parts of toluene is added and the water and organic layers separated. 102 parts of methanol is used to rinse the flask and added to the organic layer to provide a solution of 4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4,4-dimethoxybutyl]- piperidin-4-ol. Then, 59 parts of concentrated hydrochloric acid is added to a stirred solution of the organic layer to precipitate a solid. The solid is filtered, rinsed twice with 550 parts by volume portions of a 10:9:1 acetone-toluenemethanol mixture, twice with 400 parts by volume portions of a 10:l acetonemethanol mixture, and air-dried. The dried solid is then dissolved in 1,950 parts of methanol with gentle heating on a steam bath. The resulting solution is filtered and 300 parts by volume of concentrated ammonium hydroxide is added. Heating is continued to reflux and maintained thereat for about 1 hour.Then, 2,520 parts of water is added and the slurry stirred at about 75°C for 1.5 hours. After cooling to about 25°C. the solid is filtered, washed twice with 600 parts by volume portions of a 3:1 mixture of water-methanol, and airdried. The resulting product, 4-[4-chlorophenyl)-4-hydroxypiperidino]-4'- fluorobutyrophenone, is obtained in 32.5% yield. This product melts at about 148.5°C to 150.5°C.
[Brand name]

Haldol (OrthoMcNeil).
[Therapeutic Function]

Antidyskinetic, Antipsychotic
[General Description]

Haloperidol, 4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4-fluorobutyrophenone (Haldol), is anodorless white to yellow crystalline powder. Haloperidol iswell and rapidly absorbed and has a high bioavailability. It ismore than 90% bound to plasma proteins. Haloperidol is excretedslowly in the urine and feces. About 30% of a dose isexcreted in urine and about 20% of a dose in feces via biliaryelimination,and only 1% of a dose is excreted as unchangeddrug in the urine.Haloperidol is a minor substrate of CYP1A2 and a major substrate of CYP2D6 and CYP3A4.CYP2D6 inhibitors may increase the levels/effects ofhaloperidol.Haloperidol may increase the levels/effects ofCYP2D6 substrates and it may decrease the bioactivationof CYP2D6 prodrugs substrates. Haloperidol also is a moderateinhibitor of CYP2D6 and CYP3A4. CYP3A4 inducersmay decrease the levels/effects of haloperidol, whereasCYP3A4 inhibitors may increase the levels/effects ofhaloperidol. Centrally acting acetylcholinesterase inhibitorsmay increase the risk of antipsychotic-related EPS. The precisemechanism of antipsychotic action is unclear but isconsidered to be associated with the potent DA D2receptor–blocking activity in the mesolimbic system and theresulting adaptive changes in the brain. Haloperidol is usedprimarily for the long-term treatment of psychosis and is especiallyuseful in patients who are noncompliant with theirdrug treatment.
[General Description]

Haloperidol, 4[4-(p-chlorophenyl)-4-hydroxypiperidone]-4' -n-fluorobutyrophenone (Haldol),the representative of several related classes of aromaticbutylpiperidine derivatives, is a potent antipsychotic usefulin schizophrenia and in psychoses associated with braindamage. It is frequently chosen as the agent to terminatemania and often used in therapy for Gilles de la Tourettesyndrome. Haloperidol-induced dyskinesias may involveneurotoxicological metabolite similar to dopaminergic toxicantMPP+.
[Pharmaceutical Applications]

Haloperidol is an analogue of the dopamine D2 receptor antagonist and is an older antipsychotic drug. The drug is used in the treatment of schizophrenia, a neuropsychiatric disorder. In general, antipsychotic drugs work by blocking the dopamine D2 receptors.
Haloperidol is such an antipsychotic drug, which was developed in the 1950s and entered the clinic soon after that. Its use is limited by the high incidence of extrapyramidal symptoms (movement disorders caused by drugs affecting the extrapyramidal system, a neural network which is part of the motor system). Nevertheless, haloperidol may be used for the rapid control of hyperactive psychotic states and is popular for treating restlessness in the elderly.
[Biological Activity]

Dopamine antagonist with selectivity for D 2 -like receptors (K i values are 1.2, ~ 7, 2.3, ~ 80 and ~ 100 nM for D 2 , D 3 , D 4 , D 1 and D 5 receptors respectively). Subtype-selective NMDA antagonist.
[Chemical Synthesis]

Haloperidol, 4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone (6.3.8), is synthesized by the alkylation of 4-(4-chlorophenyl)-4-hydroxypiperidine (6.3.7) using 4′-chloro-4-fluorobutyrophenone (6.3.4). 4-(4-Chlorophenyl) -4-hydroxypiperidine (6.3.7) is synthesized from 2-(4-chlorophenyl)propene, which on reaction with formaldehyde and ammonium chloride gives the intermediate 4-methyl-4-(4-chlorophenyl)-1, 3-oxazine (6.3.5), evidently through stages postulated for the Prince reaction. Treatment of the resulting product with hydrochloric acid leads to the formation of 4-(4-chlorophenyl)-1,2,3,6- tetrahydropiperidine (6.3.6), probably through a stage of opening of the hydrogenated 1,3-oxazine ring, followed by dehydration, and subsequent recyclization. Addition of hydrogen bromide to the double bond of 4-(4-chlorophenyl)1,2,3,6-tetrahydropipidine (6.3.6) and the subsequent alkaline hydrolysis of the 4-(4-chlorophenyl)-4-bromopiperidine formed during the reaction, gives 4-(4-chlorophenyl)-4-hydroxypiperidine (6.3.7), the reaction of which with 4′-chloro-4-fluorobutyrophenone (6.3.4) gives the desired haloperidol (6.3.6) [41–46].

Spectrum DetailBack Directory
[Spectrum Detail]

Haloperidol(52-86-8) IR1
Haloperidol(52-86-8) 13C NMR
Haloperidol(52-86-8) MS
Haloperidol(52-86-8) IR2
Haloperidol(52-86-8) 1H NMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

52-86-8(sigmaaldrich)
[TCI AMERICA]

Haloperidol,>98.0%(LC)(T)(52-86-8)
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