Haloperidol

Base Information

• Chemical Name: Haloperidol
• CAS No.: 52-86-8
• Molecular Formula: C21H23ClFNO2
• Molecular Weight: 375.871
• Hs Code.: 2933399090
• European Community (EC) Number: 200-155-6
• NSC Number: 757054,615296,170973
• UNII: J6292F8L3D
• DSSTox Substance ID: DTXSID4034150
• Nikkaji Number: J1.365J
• Wikipedia: Haloperidol
• Wikidata: Q251347
• NCI Thesaurus Code: C537
• RXCUI: 5093
• Pharos Ligand ID: GKRULT6FAR97
• Metabolomics Workbench ID: 42846
• ChEMBL ID: CHEMBL54
• Mol file: 52-86-8.mol

Synonyms:Butyrophenone,4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4'-fluoro- (6CI,8CI);4-(4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone;4-(4-Hydroxy-4'-chloro-4-phenylpiperidino)-4'-fluorobutyrophenone;Aloperidin;Bioperidolo;Brotopon;Dozic;Einalon S;Eukystol;Haldol;Haloperin;Keselan;McN-JR 1625;NSC 615296;Peluces;Serenace;Serenelfi;g-[4-(p-Chlorphenyl)-4-hydroxypiperidino]-p-fluorbutyrophenone;

Chemical Property of Haloperidol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 5.07E-12mmHg at 25°C
• Melting Point: 152 °C
• Boiling Point: 529.034 °C at 760 mmHg
• PKA: 8.3(at 25℃)
• Flash Point: 273.75 °C
• PSA: 40.54000
• Density: 1.239 g/cm³
• LogP: 4.36350
• Storage Temp.: Store at RT
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.39 mg/m
• Water Solubility.: 2.058mg/L(22.5 oC)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 375.1401348
• Heavy Atom Count: 26
• Complexity: 451

Purity/Quality:

99% ^*data from raw suppliers

Haloperidol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 60-61-25-36/37/38-43-39/23/24/25-23/24/25-11
• Safety Statements: 53-26-36/37/39-45-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: C1CN(CCC1(C2=CC=C(C=C2)Cl)O)CCCC(=O)C3=CC=C(C=C3)F
• Recent ClinicalTrials: Quetiapine Versus Haloperidol in the Management of Hyperactive Delirium
• Recent EU Clinical Trials: Cognitive effects of adjuntive Vortioxetine in early Schizophrenia
• Recent NIPH Clinical Trials: A randomized, double-blind, adjustable-dose, parallel-group study of haloperidol or aripiprazole for the treatment of Anxiety-Depressed Attack
• Description: Haloperidol is a butyrophenone with a long duration of action. It has lile α- adrenoceptor blocking activity and minimal effect on the cardiovascular system. It is an effective antiemetic but has a high incidence of extrapyramidal adverse effects. Haloperidol may be used in the short-term management of the acutely agitated patient (when sinister causes of confusion such as hypoxaemia and sepsis have been excluded) and in the management of delirium in ICU. The duration of action of haloperidol is approximately 24–48h.
• 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. Haloperidol has been used:in ethanol to serves as an inhibitor of Erg2pto address the mechanism of haloperidol in ferroptosis using hepatocellular carcinoma cells: Hep G2 and Huh-7 cell linesin receptor internalization assayas an antipsychotic drug in Dulbecco′s Modified Eagle medium
• Therapeutic Function: Antidyskinetic, Antipsychotic
• Clinical Use: Sedative in severe anxiety Intractable hiccup Motor tics Nausea and vomiting Schizophrenia and other psychoses
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effects. Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids; possibly severe drowsiness with indometacin or acemetacin; increased risk of ventricular arrhythmias with methadone. Anti-arrhythmics: increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval; increased risk of ventricular arrhythmias with amiodarone or disopyramide - avoid. Antibacterials: increased risk of ventricular arrhythmias with moxifloxacin and delamanid - avoid with moxifloxacin; concentration reduced by rifampicin. Antidepressants: increased risk of ventricular arrhythmias with citalopram, escitalopram and tricyclics - avoid; concentration increased by fluoxetine and venlafaxine and possibly fluvoxamine; possible increased risk of convulsions with vortioxetine; concentration of tricyclics increased. Antiepileptics: metabolism increased by carbamazepine, phenobarbital and primidone; lowered seizure threshold; concentration reduced by fosphenytoin and phenytoin. Antifungals: concentration possibly increased by itraconazole. Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol; possible increased risk of ventricular arrhythmias with mefloquine or quinine - avoid. Antipsychotics: avoid concomitant use of depot formulations with clozapine (cannot be withdrawn quickly if neutropenia occurs); increased risk of ventricular arrhythmias with sulpiride and droperidol and possibly risperidone - avoid with droperidol; concentration possibly increased by chlorpromazine. Antivirals: concentration possibly increased with ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid. Anxiolytics and hypnotics: increased sedative effects; concentration increased by alprazolam and buspirone. Atomoxetine: increased risk of ventricular arrhythmias. Beta-blockers: increased risk of ventricular arrhythmias with sotalol. Cytotoxics: increased risk of ventricular arrhythmias with bosutinib, ceritinib and vandetanib - avoid with vandetanib; increased risk of ventricular arrhythmias with arsenic trioxide. Lithium: increased risk of extrapyramidal side effects and possibly neurotoxicity.

Technology Process of Haloperidol

There total 25 articles about Haloperidol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-(4-chlorophenyl)-1-<4-(4-nitrophenyl)-4-oxobutyl>-4-piperidinol (150717-69-4) → haloperidol (52-86-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In dimethyl sulfoxide; at 160 ℃; for 0.166667h; Inert atmosphere; Microwave irradiation; Anhydrous conditions;

DOI:10.1016/j.tetlet.2010.02.042

Reference yield: 88.0%

4-(4-chlorophenyl)-4-hydroxypiperidine (39512-49-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2,41167-07-1) → haloperidol (52-86-8)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; at 75 ℃; for 24h; Temperature;

Reference yield: 65.0%

4-<4-(4-chlorophenyl)-4-hydroxypiperidino>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane (56660-99-2) → haloperidol (52-86-8)

Guidance literature:

With hydrogenchloride; In methanol; for 6h; Heating;

DOI:10.1021/jm00147a035

upstream raw materials:

4-(4-chlorophenyl)-4-hydroxypiperidine

4-(4-fluorophenyl)-4-oxo-n-butyl chloride

4-<4-(4-chlorophenyl)-4-hydroxypiperidino>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane

Chlorohaloperidol

Downstream raw materials:

4-fluorobenzaldehyde

1-(4-fluorophenyl)ethanone

1-(4-fluorophenyl)but-3-en-1-one

chlorobenzene

Refernces

• 1、 -. "Preparation method of flupiperidinol". Paragraph 0089; 0096-0098; 0105-0106; 0110-0112. . Retrieved 2021/03/24.
• 2、 Chen, Guangying,Cheng, Gui-Juan,Guo, Bin,Li, Xiaobao,Ran, Chongzhao,Wang, Lu,Wang, Ting,Wei, Jun-Jie,Zheng, Caijuan,Zheng, Chao. "Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis". . p. 7543 - 7551. Retrieved 2020/08/21.