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M5435

Sigma-Aldrich

6-Methyl-2-(phenylethynyl)pyridine hydrochloride

≥98% (HPLC)

Synonym(s):

MPEP hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C14H11N · HCl
CAS Number:
Molecular Weight:
229.70
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

off-white to light tan

solubility

DMSO: 10 mg/mL, clear

storage temp.

room temp

SMILES string

Cl.Cc1cccc(n1)C#Cc2ccccc2

InChI

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

InChI key

PKDHDJBNEKXCBI-UHFFFAOYSA-N

Gene Information

General description

GRIN2B (glutamate ionotropic receptor NMDA type subunit 2B) codes for N-methyl d-aspartate receptor subtype 2B (GluN2B). It belongs to the N-methyl-D-aspartate receptor (NMDAR) gene family. It is located on chromosome 12p13.1.

Application

6-Methyl-2-(phenylethynyl)pyridine hydrochloride has been used to investigate whether 3, 4 (±) methylenedioxymethamphetamine (MDMA) could influence self-renewal via the mGlu5 receptor in mouse embryonic stem cells (mESCs).

Biochem/physiol Actions

GRIN2B (glutamate ionotropic receptor NMDA type subunit 2B) plays an important role in the growth of neurons and is highly essential for learning and memory. GRIN2B mutation is associated with neuropsychiatric and developmental disorders like schizophrenia, Parkinson′s disease and bipolar disorder. MPEP (2-methyl-6-(phenylethynyl)pyridine hydrochloride) is used to treat Alzheimer′s disease (AD).
Highly selective, non-competitive mGluR5 metabotropic glutamate receptor antagonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (G Protein Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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F Gasparini et al.
Neuropharmacology, 38(10), 1493-1503 (1999-10-26)
In the present paper we describe 2-methyl-6-(phenylethynyl)-pyridine (MPEP) as a potent, selective and systemically active antagonist for the metabotropic glutamate receptor subtype 5 (mGlu5). At the human mGlu5a receptor expressed in recombinant cells, MPEP completely inhibited quisqualate-stimulated phosphoinositide (PI) hydrolysis
A 12p13 GRIN2B deletion is associated with developmental delay and macrocephaly
Morisada N, et al.
Human Genome Variation, 16029-16029 (2016)
2-Methyl-6-(phenylethynyl) pyridine Hydrochloride Modulates Metabotropic Glutamate 5 Receptors Endogenously Expressed in Zebrafish Brain
Albasanz J L, et al.
ACS Chemical Neuroscience, 7(12), 1690-1697 (2016)
Human GRIN2B variants in neurodevelopmental disorders
Hu C, et al.
Journal of Pharmacological Sciences, 132(2), 115-121 (2016)
Mélanie Cavalier et al.
Neurochemical research, 44(3), 609-616 (2018-01-22)
Maternal immune challenge has proved to induce moderate to severe behavioral disabilities in the offspring. Cognitive/behavioral deficits are supported by changes in synaptic plasticity in different brain areas. We have reported previously that prenatal exposure to bacterial LPS could induce

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