Risperidone

Base Information

• Chemical Name: Risperidone
• CAS No.: 106266-06-2
• Molecular Formula: C23H27FN4O2
• Molecular Weight: 410.491
• Hs Code.: 29333990
• European Community (EC) Number: 600-733-1
• NSC Number: 759895
• UNII: L6UH7ZF8HC
• DSSTox Substance ID: DTXSID8045193
• Nikkaji Number: J138.382E
• Wikipedia: Risperidone
• Wikidata: Q412443
• NCI Thesaurus Code: C29416
• RXCUI: 35636
• Pharos Ligand ID: HBTADUAJZ6D9
• Metabolomics Workbench ID: 38706
• ChEMBL ID: CHEMBL85
• Mol file: 106266-06-2.mol

Synonyms:Consta, Risperdal;R 64,766;R 64766;R-64,766;R-64766;R64,766;R64766;Risperdal Consta;Risperidal;Risperidone

Chemical Property of Risperidone

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 4.14E-13mmHg at 25°C
• Melting Point: 170 °C
• Refractive Index: 1.676
• Boiling Point: 572.4 °C at 760 mmHg
• PKA: pKa 8.3 (Uncertain)
• Flash Point: 300 °C
• PSA: 64.16000
• Density: 1.383 g/cm³
• LogP: 3.52830
• Storage Temp.: Room temp
• Solubility.: DMSO: ≥5mg/mL
• Water Solubility.: 44.74mg/L(25 oC)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 410.21180428
• Heavy Atom Count: 30
• Complexity: 731

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Risperidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 25-39/23/24/25-23/24/25-11
• Safety Statements: 28-36-45-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: CC1=C(C(=O)N2CCCCC2=N1)CCN3CCC(CC3)C4=NOC5=C4C=CC(=C5)F
• Recent ClinicalTrials: Efficacy and Safety of MK-8189 in Participants With an Acute Episode of Schizophrenia (MK-8189-008)
• Recent EU Clinical Trials: Individualized care with antipsychotics in patients suffering from schizophrenia spectrum disorders-
• Recent NIPH Clinical Trials: Hyperbaric oxygen therapy versus Risperidone in autistic children: a comparative study
• Uses: 1. It has antagonism effect on 5HT2 receptors and D2 receptors. It is used for acute and chronic schizophrenia. 2. Antipsychotic drugs. Risperidone has been used:to study its effects on bone formation and differentiationto investigate the relationship between risperidone (RIS) dosages and RIS plasma levels in autism spectrum disorder (ASD) pediatric patientsto reverse induced schizophrenia-like behavior in mice neuroprotectant, inhibitory neurotransmitter, GABA agonist For the treatment of schizophrenia in adults and in adolescents, ages 13 to 17, and for the short-term treatment of manic or mixed episodes of bipolar I disorder in children and adolescents ages 10 to 17. May also be used to manage symptoms of inappropria A combined serotonin (5-HT2) and dopamine (D2) receptor antagonist
• production method: 1-Acetyl-4-methyl-piperidine chloride and difluorobenzene react under aluminum trichloride catalysis, after acylation, use hydrochloric acid hydrolysis to deacetylate in piperidine ring, and then after hydroxylamine ,use base to catalyze, after cyclization , get benzisoxazole derivatives. 4.4 parts of the isoxazole derivatives, 5.3 parts of ethyl 3-chloro-2-methyl-4H-pyrido [1,2-α] pyrimidin-4-one hydrochloride, 8 parts of sodium carbonate and 0.1 parts of potassium iodide, in dimethyl formamide , heat at 85-90 ℃, Risperidone is generated, 46% yield.
• Description: Risperidone is a novel antipsychotic introduced for the treatment of acute and chronic schizophrenia. It has a balanced serotonin 5-HT2 and dopamine D2 receptor antagonist activity. While the anti-D2 activity may relate to the antipsychotic potency of neuroleptic agents, an antidepressive efficacy of substances with anti-5-HT2 activity has been suggested. Risperidone, therefore, has therapeutic action on both positive and negative symptoms of schizophrenia and produces significantly fewer side effects especially extrapyramidal symptoms compared with commonly used pure D2 antagonist antipsychotics. It also has potential for management of alcohol withdrawal and cocaine addiction.
• Clinical Use: Schizophrenia Psychoses Mania Persistent aggression in Alzheimer’s dementia
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids; increased risk of ventricular arrhythmias with methadone - avoid. Antidepressants: concentration increased by fluoxetine and possibly paroxetine; concentration of tricyclics possibly increased. Antiepileptics: antagonism, convulsive threshold may be lowered; metabolism accelerated by carbamazepine. Antimalarials: avoid with artemether with lumefantrine; possible increased risk of ventricular arrhythmias with mefloquine and quinine. Antipsychotics: possible increased risk of ventricular arrhythmias with other antipsychotics that prolong the QT interval; avoid concomitant use of depot formulations with clozapine (cannot be withdrawn quickly if neutropenia occurs). Antivirals: ritonavir may increase concentration of risperidone. Anxiolytics and hypnotics: enhanced sedative effects. Atomoxetine: increased risk of ventricular arrhythmias. Beta blockers: possible increased risk of ventricular arrhythmias with sotalol. Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide. Lithium: increased risk of extra-pyramidal side effects and possible neurotoxicity.

Technology Process of Risperidone

There total 23 articles about Risperidone 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: 94.9%

C23H28F2N4O2 (132961-05-8) → Risperidone (106266-06-2)

Guidance literature:

With borax; sodium hydroxide; In ethanol; at 70 ℃; for 0.5h;

Reference yield: 93.6%

3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride (93076-03-0) + 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride (84163-13-3) → Risperidone (106266-06-2)

Guidance literature:

With sodium carbonate; In methanol; at 73 - 75 ℃; for 4 - 4.5h; Product distribution / selectivity;

Reference yield: 93.2%

3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (63234-80-0) + 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride (84163-13-3) → Risperidone (106266-06-2)

Guidance literature:

With sodium carbonate; In water; at 110 - 120 ℃; for 0.666667h; Product distribution / selectivity;

upstream raw materials:

3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole

3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride

(2,4-difluorophenyl)(4-piperidinyl)methanone oxime

Downstream raw materials:

risperidone dihydrochloride

C₂₃H₂₇FN₄O₂*C₆H₃N₃O₇

C₂₃H₂₇FN₄O₂*C₈Cl₂N₂O₂

C₂₃H₂₇FN₄O₂*C₁₂H₄N₄

Refernces

• 1、 El-Habeeb, Abeer A.,Al-Saif, Foziah A.,Refat, Moamen S.. "Spectroscopic and thermal investigations on the charge transfer interaction between risperidone as a schizophrenia drug with some traditional π-acceptors: Part 2". . p. 464 - 477. Retrieved 2013/04/23.
• 2、 -. "PROCESS FOR PREPARING RISPERIDONE". Page/Page column 5. . Retrieved 2009/07/18.