346688-38-8

Basic information

• Product Name: 4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine
• Synonyms: 4-(3-Methylsulfonylphenyl)-1-propylpiperidine;4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine;ACR 16;4-(3-Methanesulfonyl-phenyl)-1-propyl-piperidine;Acr16 compound;Piperidine, 4-(3-(methylsulfonyl)phenyl)-1-propyl-;ASP 2314;FR 310826
• CAS NO: 346688-38-8
• Molecular Formula: C15H23NO2S
• Molecular Weight: 281.42
• Product Categories: Aromatics;Heterocycles;Neurochemicals;Sulfur & Selenium Compounds
• Mol File: 346688-38-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 73-750C
• Boiling Point: 434.205°C at 760 mmHg
• Flash Point: 216.4°C
• Appearance: /
• Density: 1.093g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Soluble in DMSO (up to 10 mg/ml).
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: 4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine(346688-38-8)
• EPA Substance Registry System: 4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine(346688-38-8)

Safety Data

• Hazardous Substances Data: 346688-38-8(Hazardous Substances Data)

Usage

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

Chemical Properties

4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine is Off-White Solid

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.

References

1) Pettersson (2010),?Synthesis and Evaluation of a Set of 4-Phenylpiperidines and 4-Phenylpiperazines as D2 Receptor Ligands and the Discovery of the Dopaminergic Stabilizer 4-[3-(Methylsulfonyl)phenyl]-1-propylpiperidine (Huntexil, Pridopidine, ACR16);?J.Med.Chem.?53?2510 2)?The dopamine stabilizers (S)-(-)-(3-methanesulfonylphenyl)-1-propyl-piperidine [(-)-OSU6162] and 4-(3-methanesulfonylphenyl)-1-propyl-piperidine (ACR16) show high in vivo D2 receptor occupancy, antipsychotic-like efficacy, and low potential for motor side effects in the rat;?J.Pharmacol.Exp.Ther.?318?810 3) Dyhring?et al.?(2010)?The dopaminergic stabilizers pridopidine (ACR16) and (-)-OSU6162 display dopamine D(2) receptor antagonism and fast receptor dissociation properties;?Eur.J.Pharmacol.?628?19 4) Sahlholm (2015)?Pridopidine selectively occupies sigma-1 rather than dopamine D2 receptors at behaviorally active doses;?Psychopharmacology (Berl)?232?3443 5)?Sahlholm?et al.?(2013),?The dopamine stabilizers ACR16 and (-)-OSU6162 display nanomolar affinities at the?s-1 receptor;?Mol.Psychiatry?18?12 6) Francardo?et al.?(2019),?Pridopidine Induces Functional Neurorestoration Via the Sigma-1 Receptor in a Mouse Model of Parkinson’s Disease;?Neurotherapeutics?16?465 7) Ryskamp,?et al.?(2017),?The sigma-1 receptor mediates the beneficial effects of pridopidine in a mouse model of Huntington disease;?Neurobiol.Dis.?97(Pt A)?46 8) Ionescu?et al.?(2019),?Targeting the Sigma-1 Receptor via Pridopidine Ameliorates Central Features of ALS Pathology in a SOD1G93A Model;?Cell Death Dis.?10?210

InChI:InChI=1/C15H23NO2S/c1-3-9-16-10-7-13(8-11-16)14-5-4-6-15(12-14)19(2,17)18/h4-6,12-13H,3,7-11H2,1-2H3

Upstream product

• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 882737-41-9 4-hydroxy-4-(3-(methylthio)phenyl)-1-propylpiperidin-1-ium chloride 
• 882737-40-8 4-(3-(methylthio)phenyl)-1-propylpiperidin-4-ol 

Downstream Products

• 1440284-30-9 4-(3-methanesulfonylphenyl)-1-propylpiperidine hydrobromide 

Relevant articles and documents

Practical synthesis of pharmaceutically relevant molecules enriched in sp3 character

The expedient synthesis of compounds enriched in sp3 character is key goal in modern drug discovery. Herein, we report how a single pot Suzuki-Miyaura-hydrogenation can be used to furnish lead and fragment-like products in good to excellent yields. The approach has been successfully applied in formats amenable to parallel synthesis, in an asymmetric sense, and in the preparation of molecules with annotated biological activity.

PROCESS FOR THE SYNTHESIS OF 4-(3-METHANESULFONYLPHENYL)-1-N-PROPYL-PIPERIDINE

The present invention is directed to processes for the preparation of 4-(3-methanesulfonyl-phenyl)-1-N-propylpiperidine (I) or a pharmaceutically acceptable salt thereof, which comprises: oxidizing a sulfide of the formula (II): with a catalytic oxidizing