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gamma-(4-(p-Chlorphenyl)4-hydroxy-piperidino)-p-fluorbutyrophenon Produkt Beschreibung

Haloperidol Struktur
52-86-8
CAS-Nr.
52-86-8
Bezeichnung:
gamma-(4-(p-Chlorphenyl)4-hydroxy-piperidino)-p-fluorbutyrophenon
Englisch Name:
Haloperidol
Synonyma:
ALDO;Dozic;Halol;r1625;Haldol;Linton;Pernox;R 1625;Sernas;Sernel
CBNumber:
CB7774829
Summenformel:
C21H23ClFNO2
Molgewicht:
375.86
MOL-Datei:
52-86-8.mol

gamma-(4-(p-Chlorphenyl)4-hydroxy-piperidino)-p-fluorbutyrophenon Eigenschaften

Schmelzpunkt:
152 °C
Siedepunkt:
529.0±50.0 °C(Predicted)
Dichte
1.1820 (estimate)
Flammpunkt:
9℃
storage temp. 
2-8°C
Löslichkeit
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.39 mg/mL
Aggregatzustand
powder
pka
8.3(at 25℃)
Farbe
white
Wasserlöslichkeit
2.058mg/L(22.5 ºC)
Merck 
14,4598
CAS Datenbank
52-86-8(CAS DataBase Reference)
NIST chemische Informationen
Haloperidol(52-86-8)
EPA chemische Informationen
Haloperidol (52-86-8)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T,F
R-Sätze: 60-61-25-36/37/38-43-39/23/24/25-23/24/25-11
S-Sätze: 53-26-36/37/39-45-36/37-16
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS-Nr. EU1575000
HazardClass  6.1(b)
PackingGroup  III
HS Code  2933399090
Giftige Stoffe Daten 52-86-8(Hazardous Substances Data)
Toxizität LD50 orally in rats: 165 mg/kg (Goldenthal); i.p. in mice: 60 mg/kg (Collins, Horlington)
Bildanzeige (GHS)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
H360 Kann die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Fertility (Fruchtbarkeit) Kategorie 1 Achtung
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H370 Schädigt die Organe. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 1 Achtung P260, P264, P270, P307+P311, P321,P405, P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P261 Einatmen von Staub vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P311 GIFTINFORMATIONSZENTRUM/Arzt anrufen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P333+P313 Bei Hautreizung oder -ausschlag: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

gamma-(4-(p-Chlorphenyl)4-hydroxy-piperidino)-p-fluorbutyrophenon Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R60:Kann die Fortpflanzungsfähigkeit beeinträchtigen.
R61:Kann das Kind im Mutterleib schädigen.
R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R43:Sensibilisierung durch Hautkontakt möglich.

S-Sätze Betriebsanweisung:

S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

Chemische Eigenschaften

White Crystalline Powder

Originator

Haldol,Janssen-Le Brun,France,1960

Verwenden

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.

Verwenden

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.

Trademarks

Haldol (OrthoMcNeil).

Therapeutic Function

Antidyskinetic, Antipsychotic

Allgemeine Beschreibung

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.

Allgemeine Beschreibung

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+.

Pharmazeutische Anwendungen

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.

Biologische Aktivität

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].

gamma-(4-(p-Chlorphenyl)4-hydroxy-piperidino)-p-fluorbutyrophenon Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


gamma-(4-(p-Chlorphenyl)4-hydroxy-piperidino)-p-fluorbutyrophenon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 207)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Target Molecule Corp
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Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8910 55
Guangzhou PI PI Biotech Inc
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 739 60
SHANDONG ZHI SHANG CHEMICAL CO.LTD
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18853181302
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BOC Sciences
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1-631-614-7828 inquiry@bocsci.com United States 19752 58
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47498 58

52-86-8(gamma-(4-(p-Chlorphenyl)4-hydroxy-piperidino)-p-fluorbutyrophenon)Verwandte Suche:


  • Einalon
  • 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
  • 4'-Fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)butyrophenone
  • 4'-Fluoro-4-(4-hydroxy-4-(4'-chlorophenyl)piperidino)butyrophenone
  • ALDO
  • Aloperidin
  • Aloperidol
  • Aloperidolo
  • Aloperidon
  • Bioperidolo
  • Brotopon
  • Butyrophenone, 4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4'-fluoro-
  • Butyrophenone, 4'-fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-
  • Dozic
  • Einalon S
  • einalons
  • Eukystol
  • fortunan
  • Galoperidol
  • gamma-(4-(p-Chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenone
  • gamma-(4-(p-chlorophenyl)-4-hydroxypiperidino)-p-fluorbutyrophenone
  • gamma-(4-(p-chlorophenyl)-4-hydroxypiperidino)-p-fluorobutyrophenone
  • Haldol
  • Halidol
  • Halojust
  • Halol
  • Halopal
  • Halopidol
  • Halopoidol
  • Halosten
  • Keselan
  • Lealgin compositum
  • lealgincompositum
  • Linton
  • McM-JR-1625
  • McN-JR-1625
  • Mixidol
  • Pekuces
  • Peluces
  • Pernox
  • R 1625
  • HALOPERIDOL,USP
  • 4-(p-Chlorophenyl)-1-[4-(p-fluorophenyl)-4-hydroxybutyl]piperidin-4-ol
  • 4-[4-(4-Chlorophenyl)-4-hydroxypiperidine-1-yl]-1-(4-fluorophenyl)butane-1-ol
  • Dihydrohaloperidol
  • Haloperidol【reduced】
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