Pridopidine

Base Information

• Chemical Name: Pridopidine
• CAS No.: 346688-38-8
• Molecular Formula: C15H23NO2S
• Molecular Weight: 281.41
• Hs Code.: 2933399090
• European Community (EC) Number: 810-806-1
• UNII: HD4TW8S2VK
• DSSTox Substance ID: DTXSID90188225
• Nikkaji Number: J2.566.160E
• Wikipedia: Pridopidine
• Wikidata: Q7242858
• NCI Thesaurus Code: C170349
• Pharos Ligand ID: NLQVHYLRA3T7
• Metabolomics Workbench ID: 153021
• ChEMBL ID: CHEMBL596802
• Mol file: 346688-38-8.mol

Synonyms:4-(3-(methylsulfonyl)phenyl)-1-propylpiperidine;4-(3-methanesulfonylphenyl)-1-propylpiperidine;ACR16 compound;huntexil;pridopidine

Chemical Property of Pridopidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 73-750C
• Refractive Index: 1.526
• Boiling Point: 434.205°C at 760 mmHg
• Flash Point: 216.4°C
• PSA: 45.76000
• Density: 1.093g/cm³
• LogP: 3.69820
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Soluble in DMSO (up to 10 mg/ml).
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 281.14495015
• Heavy Atom Count: 19
• Complexity: 366

Purity/Quality:

98%Min ^*data from raw suppliers

4-(3-Methylsulfonylphenyl)-1-propylpiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1CCC(CC1)C2=CC(=CC=C2)S(=O)(=O)C
• Recent ClinicalTrials: HEALEY ALS Platform Trial - Regimen D Pridopidine
• Recent EU Clinical Trials: A Phase 3, Randomized, Double-Blind, Placebo-Controlled, Parallel Arm, Multicenter Study Evaluating the Efficacy and Safety of Pridopidine in Patients with Early Stage of Huntington Disease
• Description: Pridopidine (346688-38-8) is being studied as a potential treatment for Huntington’s disease, Parkinson’s disease, and schizophrenia based on its locomotor stabilizing and antipsychotic-like effects.1,2?It was, unusually, able to reverse both hypo- and hyperdopaminergia depending on local dopamine concentrations without inducing catalepsy. This was originally attributed to functional dopamine D2 antagonism with fast on/off kinetics (“dopamine stabilizer”).3?More recent studies have attributed pridopidine’s effects to its being a more potent sigma-1 ligand than a D2 ligand.4,5?Displays neuroprotective/restorative effects6,7?and ameliorates central features of amyotrophic lateral sclerosis pathology8?in a sigma-1-mediated manner
• Uses: 4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine is a new modulator of dopamine neurotransmission. Dopamine is a neurotransmitter in the brain. Drugs that act at central dopamine receptors are commonly used in the treatment of neurologic and psychiatric disorders.

Technology Process of Pridopidine

There total 4 articles about Pridopidine 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: 95.0%

→ Pridopidine (346688-38-8)

Guidance literature:

With formic acid; palladium 10% on activated carbon; In Isopropyl acetate; water; at 20 ℃; for 16 - 24h;

Reference yield:

4-(3-(methylthio)phenyl)-1-propylpiperidin-4-ol (882737-40-8) → Pridopidine (346688-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfuric acid / toluene / 3 h / 45 - 80 °C

1.2: 2.33 h / 25 - 55 °C

2.1: formic acid / water / 10 - 20 °C

2.2: 5 - 35 °C / Inert atmosphere

With formic acid; sulfuric acid; In water; toluene;

Reference yield:

4-hydroxy-4-(3-(methylthio)phenyl)-1-propylpiperidin-1-ium chloride (882737-41-9) → Pridopidine (346688-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfuric acid / toluene / 83 - 111 °C

1.2: 55 °C

2.1: formic acid / water / 10 - 20 °C

2.2: 5 - 35 °C / Inert atmosphere

With formic acid; sulfuric acid; In water; toluene;

upstream raw materials:

4-(3-(methylthio)phenyl)-1-propylpiperidin-4-ol

4-hydroxy-4-(3-(methylthio)phenyl)-1-propylpiperidin-1-ium chloride

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Downstream raw materials:

4-(3-methanesulfonylphenyl)-1-propylpiperidine hydrobromide