1627-30-1

Basic information

• Product Name: 4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE
• Synonyms: 4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE;AIDS125025;4-methyl-1,2,4-triazine-3,5(2H,4H)-dione
• CAS NO: 1627-30-1
• Molecular Formula: C₄H₅N₃O₂
• Molecular Weight: 127.1014
• Mol File: 1627-30-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.54g/cm³
• Refractive Index: 1.651
• CAS DataBase Reference: 4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE(1627-30-1)
• EPA Substance Registry System: 4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE(1627-30-1)

Safety Data

• Hazardous Substances Data: 1627-30-1(Hazardous Substances Data)

Usage

General Description

4-Methyl-2H-[1,2,4]triazine-3,5-dione, also known as N-methylbarbituric acid, is a chemical compound belonging to the class of triazines. It is commonly used as a precursor to various pharmaceuticals, including barbiturates, which are central nervous system depressants. 4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE has the potential to act as a sedative, hypnotic, and anticonvulsant, making it a useful building block in the synthesis of drugs that affect the central nervous system. Additionally, it has been studied for its potential antimicrobial and anticancer properties. However, it is important to handle this chemical with caution, as it can be toxic and should only be used by trained professionals in a laboratory setting.

InChI:InChI=1/C4H5N3O2/c1-7-3(8)2-5-6-4(7)9/h2H,1H3,(H,6,9)

Upstream product

• 4338-50-5 2-acetyl-2H,3H,4H,5H-[1,2,4]-triazin-3,5-dione 
• 74-88-4 methyl iodide 
• 104-15-4 toluene-4-sulfonic acid 
• 88512-99-6 2-acetyl-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione 

Relevant articles and documents

Synthesis, in vitro and in vivo evaluation of [O-methyl-11C] 2-{4-[4-(3-methoxyphenyl)piperazin-1-yl]-butyl}-4-methyl-2H-[1,2,4]-triazine-3, 5-dione: A novel agonist 5-HT1A receptor PET ligand

Synthesis and in vivo evaluation of 2-{4-[4-(3-methoxyphenyl)piperazin-1- yl]-butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione (5 or MMT), a high affinity and selective serotonin 5-HT1AR agonist PET tracer, are described. GTPγS assay shows that MMT

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 in vivo validation of [O-methyl-11C]2-{4-[4-(7- methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3, 5-dione: A novel 5-HT1A receptor agonist positron emission tomography ligand

Antagonist 5-HT1A PET ligands are available, but an agonist ligand would give more information about signal transduction capacity. Synthesis and in vivo evaluation of [O-methyl-11C]2-{4-[4-(7- methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3, 5-dione (10), a potential high affinity (Ki = 1,36 nM) 5-HT 1A agonist PET tracer is described. Piperazine 10 is a 5-HT 1A agonist with an EC50 comparable to serotonin, based on cAMP formation and GTPγS binding assays. Radiosynthesis of [ 11C]10 has been achieved by reacting 2-{4-[4-(7-hydroxynaphthalen-1- yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione (9) and [ 11C]CH3OTf in 25 ± 5% (n = 15) yield at the end of synthesis (EOS). The chemical and radiochemical purities of [11C]10 were >99% with a specific activity 1500 ± 300 Ci/mmol (n = 15). PET studies in anesthetized baboon demonstrate [11C]10 specific binding in brain regions rich in 5-HT1A receptors. Binding of [ 11C]10 was blocked by WAY100635 and 8-OH-DPAT. The regional brain volumes of distribution (VT) of [11C]10 in baboon correlate with [11C]WAY100635 VT in baboons. These data provide evidence that [11C]10 is the first promising agonist PET tracer for the 5-HT1A receptors.