96206-92-7

Basic information

• Product Name: MPEP
• Synonyms: MPEP HYDROCHLORIDE;MPEP;6-METHYL-2-(PHENYLETHYNYL)-PYRIDINE HCL;2-METHYL-6-(PHENYLETHYNYL)PYRIDINE HYDROCHLORIDE;MPEP,HCl;2-methyl-6-(2-phenylethynyl)pyridine
• CAS NO: 96206-92-7
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 229.7
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;All Inhibitors;Inhibitors;Neurochemicals;Glutamate receptor;Glutamate
• Mol File: 96206-92-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 45-45.5 °C
• Boiling Point: 336.3°Cat760mmHg
• Flash Point: 144.8°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.000221mmHg at 25°C
• Storage Temp.: Desiccate at +4°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.97±0.12(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: MPEP(CAS DataBase Reference)
• NIST Chemistry Reference: MPEP(96206-92-7)
• EPA Substance Registry System: MPEP(96206-92-7)

Safety Data

• Hazardous Substances Data: 96206-92-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 96206-92-7 differently. You can refer to the following data:
1. A potent, subtype selective mGluR5 antagonist
2. 2-Methyl-6-(2-phenylethynyl)pyridine induces pathophysiological mGluR5 signaling in Alzheimer''s disease model mice in sex-selective manner.

Biological Activity

Potent and highly selective non-competitive antagonist at the mGlu 5 receptor subtype (IC 50 = 36 nM) and a positive allosteric modulator at mGlu 4 receptors. Centrally active following systemic administration in vivo . Reverses mechanical hyperalgesia in the inflamed rat hind paw. Also available as part of the Group I mGlu Receptor Tocriset? .

references

[1] gasparini f, lingenh?hl k, stoehr n, et al. 2-methyl-6-(phenylethynyl)-pyridine (mpep), a potent, selective and systemically active mglu5 receptor antagonist. neuropharmacology, 1999, 38(10): 1493-1503.[2] tatarczyńska e, k?odzińska a, chojnacka-wójcik e, et al. potential anxiolytic-and antidepressant-like effects of mpep, a potent, selective and systemically active mglu5 receptor antagonist. british journal of pharmacology, 2001, 132(7): 1423-1430.

InChI:InChI=1/C14H11N.ClH/c1-12-6-5-9-14(15-12)11-10-13-7-3-2-4-8-13;/h2-9H,1H3;1H

Upstream product

• 857432-57-6 2-(α,β-dibromo-phenethyl)-6-methyl-pyridine 
• 931-19-1 2-methylpyridine N-oxide 
• 5315-25-3 2-bromo-6-methylpyridine 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 656800-40-7 trimethyl-[2-(6-methyl-2-pyridyl)ethynyl]silane 
• 7714-33-2 methyl phenylethynyl sulfide 
• 637-44-5 phenylpropyolic acid 
• 18368-63-3 6-chloro-2-picoline 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 5315-24-2 1-(6-methylpyridin-2-yl)hydrazine 

Downstream Products

• 1083-25-6 2-(6-methylpyridin-2-yl)-1-phenylethanone 
• 96206-98-3 (5-Methyl-2-phenyl-indolizin-3-yl)-phenyl-methanone 
• 7370-21-0 2-methyl-6-[(E)-2-phenylethenyl]pyridine 

Relevant articles and documents

Visible-light induced copper(i)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes

Visible light mediated copper catalysed denitrogenative oxidative coupling of 2-hydrazinopyridines with terminal alkynes to form 2-(alkyl/arylethynyl) pyridines in the presence of O2 at room temperature is reported with 42 examples. This is the first report on visible light stimulated N2 elimination by an in situ generated copper(ii) superoxo/peroxo complex. N2 and water are the only by-products. The green chemistry metrics evaluation signifies that the current method is ecofriendly and economically feasible. This method allows the green synthesis of mGluR5 receptor antagonists, 2-methyl-6-(phenylethynyl)pyridine (MPEP) and 2-((3-methoxyphenyl)ethynyl)-6-methylpyridine (M-MPEP).

Palladium-catalyzed deacetonative coupling of aryl propargylic alcohols with aryl chlorides in water

A highly efficient and green process for palladium-catalyzed deacetonative coupling of aryl propargylic alcohols with aryl chlorides has been developed. The reaction occurs smoothly in neat water with 2 mol% PdCl2 as catalyst, and various synthetically useful functional groups, including ether, aldehyde, ketone, and heterocyclics, are well tolerated. Moreover, the reaction could proceed through a consecutive Sonogashira/deacetonative process using 2-methyl-3-butyn-2-ol and aryl chlorides as coupling partners, affording the symmetric alkynes in good yields.

Simultaneous rapid reaction workup and catalyst recovery

By combining reaction work-up and catalyst recovery into a simple filtration procedure we have developed a substantially faster technique for organic synthesis. Our protocol eliminates the time-consuming conventional liquid-liquid extraction and is capable of parallelization and automation. Additionally, it requires only minimal amounts of solvent.