179756-58-2

Basic information

• Product Name: EPTAPIRONE
• Synonyms: EPTAPIRONE;4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione;F 11440;4-Methyl-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2,4-triazine-3,5(2H,4H)-dione
• CAS NO: 179756-58-2
• Molecular Formula: C16H23N7O2
• Molecular Weight: 345.405
• Mol File: 179756-58-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 517.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.72±0.10(Predicted)
• CAS DataBase Reference: EPTAPIRONE(CAS DataBase Reference)
• NIST Chemistry Reference: EPTAPIRONE(179756-58-2)
• EPA Substance Registry System: EPTAPIRONE(179756-58-2)

Safety Data

• Hazardous Substances Data: 179756-58-2(Hazardous Substances Data)

Usage

Description

Eptapirone is a potent agonist of the serotonin (5-HT) receptor subtype 5-HT1A, characterized by its high selectivity and affinity for the 5-HT1A receptor over other receptor subtypes. It exhibits anxiolytic and antidepressant-like activities in preclinical models, making it a promising candidate for the treatment of anxiety and depression.

Uses

Used in Pharmaceutical Industry:
Eptapirone is used as an anxiolytic agent for its potential to alleviate anxiety symptoms by selectively targeting the 5-HT1A receptor, which is implicated in the regulation of mood and anxiety.
Eptapirone is also used as an antidepressant agent for its demonstrated ability to exhibit antidepressant-like effects in preclinical models, suggesting its potential to treat depressive disorders by modulating the serotonin system.
Additionally, Eptapirone is used in the development of drug candidates for the treatment of anxiety and depression, given its high selectivity and potency as a 5-HT1A receptor agonist, which may lead to improved therapeutic outcomes with fewer side effects compared to existing treatments.

Upstream product

• 179756-87-7 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione 
• 78069-54-2 1-(2-pyrimidinyl)piperazine hydrochloride 
• 20980-22-7 N-(2-pyridinyl)piperazine 

Relevant articles and documents

An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base

Eptapirone free base, F11440,4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione, represents a potent and selective 5-HT1A receptor agonist with high efficacy and the potential to regulate anxiety disorders. Herein, we report a method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the commercially available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50?°C for 16?h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50?°C for 12?h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the commercial availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible commercial applications.

Synthesis and evaluation of arylpiperazines derivatives of 3,5-dioxo-(2H,4H)-1,2,4-triazine as 5-HT1AR ligands

5-HT1AR agonist or partial agonists are established drug candidates for psychiatric and neurological disorders. We have reported the synthesis and evaluation of a series of high affinity 5-HT1AR partial agonist PET imaging agents with greater selectivity over α-1AR. The characteristic of these molecules are 3,5-dioxo-(2H,4H)-1,2,4-triazine skeleton tethered to an arylpiperazine unit through an alkyl side chain. The most potent 5-HT1AR agonistic properties were found to be associated with the molecules bearing C-4 alkyl group as the linker. Therefore development of 3,5-dioxo-(2H,4H)-1,2,4-triazine bearing arylpiperazine derivatives may provide high affinity selective 5-HT1AR ligands. Herein we describe the synthesis and evaluation of the binding properties of a series of arylpiperazine analogues of 3,5-dioxo-(2H,4H)-1,2,4-triazine.

3,5-dioxo-(2H,4H)-1,2,4-triazine derivatives

Novel 3,5-dioxo-(2H,4H-triazine derivatives of general formula (I): wherein R1 is hydrogen, a C1 -C4 alkyl radical, phenyl C1 -C4 alkyl or phenyl, the phenyl ring being optionally substituted by one o