138847-85-5

Basic information

• Product Name: PRE-084
• Synonyms: 2-(4-MORPHOLINETHYL)-1-PHENYLCYCLOHEXANECARBOXYLATE HCL;2-(4-MORPHOLINETHYL) 1-PHENYLCYCLOHEXANECARBOXYLATE HYDROCHLORIDE;PRE-084;PRE-084 HYDROCHLORIDE;PRE-084HCl;2-(4-morpholino)ethyl-1-phenylcyclohexane-1-carboxylate;1-Phenylcyclohexanecarboxylic acid 2-morpholinoethyl ester;4-MeO-PBP
• CAS NO: 138847-85-5
• Molecular Formula: C19H28ClNO3
• Molecular Weight: 353.88
• Product Categories: Sigma receptor;pharmaceuticals
• Mol File: 138847-85-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 446.6°Cat760mmHg
• Flash Point: 223.9°C
• Appearance: /solid
• Density: 1.103g/cm³
• Vapor Pressure: 3.61E-08mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Store at RT
• Solubility: H2O: ≤24 mg/mL
• PKA: 5.99±0.10(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: PRE-084(CAS DataBase Reference)
• NIST Chemistry Reference: PRE-084(138847-85-5)
• EPA Substance Registry System: PRE-084(138847-85-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 138847-85-5(Hazardous Substances Data)

Usage

Description

PRE-084, also known as 138847-85-8, is a selective agonist of the sigma-1 (σ1) receptor subtype with a high affinity for the σ1 receptor (IC50 of 2.2 nM) and a much lower affinity for the σ2 receptor (IC50 of 13091 nM). It has shown neuroprotective and neurorestorative effects in various brain injury and neurodegenerative conditions.

Uses

Used in Pharmaceutical Industry:
PRE-084 is used as a neuroprotective agent for its ability to demonstrate neuroprotective and neurorestorative effects in brain injury and neurodegenerative conditions. This makes it a promising candidate for the development of treatments for various neurological disorders.
Used in Research and Development:
PRE-084 is used as a research tool for studying the role of sigma-1 receptors in the central nervous system. Its high selectivity for the σ1 subtype makes it a valuable compound for investigating the specific functions and therapeutic potential of σ1 receptors in various neurological conditions.
Used in Drug Development:
PRE-084 is used as a lead compound in the development of new drugs targeting the sigma-1 receptor subtype. Its high affinity and selectivity for the σ1 receptor make it an attractive starting point for designing more potent and selective sigma-1 receptor agonists with potential therapeutic applications in neurological disorders.

Biological Activity

High affinity, selective σ 1 agonist (K i values are 2.2 and 13091 nM for σ 1 and σ 2 receptors respectively). Selective over PCP receptors (IC 50 > 100000 nM) and several other receptor systems. Produces antiamnesic and antitussive effects in vivo .

Biochem/physiol Actions

PRE-084 is a potent and highly selective σ1 opioid receptor agonist. It offers neuroprotection upon embolic stroke.

References

1) Su?et al.?(1991),?Sigma compounds derived from phencyclidine. Identification of PRE-084, a new selective sigma ligand; J. Pharmacol. Exp. Ther.?259?543 2) Griesmaier?et al.?(2012),?Neuroprotective effects of the sigma-1 receptor ligand PRE-084 against excitotoxic perinatal brain injury in newborn mice; Exp. Neurol.?237?388 3) Dong?et al.?(2016),?Sigma-1 Receptor Modulates Neuroinflammation After Traumatic Brain Injury; Cell Mol. Neurobiol.?36?639 4) Guzman-Lenis?et al.?(2009),?Selective sigma receptor agonist 2-(4-Morpholinethyl) 1-phenylcyclohexanecarboxylate (PRE084) promotes neuroprotection and neurite elongation through protein kinase C (PKC) signaling on motoneurons; Neuroscience?162?31 5) Hyrskyluoto?et al.?(2013),?Sigma-1 receptor agonist PRE084 in protective against mutant huntingtin-induced cell degeneration: involvement of calpastatin and the NF-κB pathway; Cell Death Dis.?4?e646 6) Francardo?et al.?(2014),?Pharmacological stimulation of sigma-1 receptors has neurorestorative effects in experimental parkinsonism; Brain?137(Pt7)?1998 7) Mancuso?et al.?(2012),?Sigma-1R agonist improves motor function and motoneuron survival in ALS mice; Neurotherapeutics?9?814

InChI:InChI=1/C19H27NO3/c21-18(23-16-13-20-11-14-22-15-12-20)19(9-5-2-6-10-19)17-7-3-1-4-8-17/h1,3-4,7-8H,2,5-6,9-16H2