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Details

Stereochemistry ACHIRAL
Molecular Formula C14H11N.ClH
Molecular Weight 229.705
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-METHYL-6-(PHENYLETHYNYL)PYRIDINE HYDROCHLORIDE

SMILES

Cl.CC1=CC=CC(=N1)C#CC2=CC=CC=C2

InChI

InChIKey=PKDHDJBNEKXCBI-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H11N
Molecular Weight 193.2438
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

MPEP (2-methyl-6-(phenylethynyl)pyridine) was one of the first compounds found to act a selective antagonist for the metabotropic glutamate receptor subtype mGluR5. It was under development by Novartis in the late 1990's. MPEP was found to produce neuroprotective effects following acute brain injury in animals. MPEP was also found to have positive effects on animal models of depression, anxiety and morphine withdrawl.

CNS Activity

Curator's Comment: referenced study was conducted on mice

Originator

Curator's Comment: # Novartis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P41594
Gene ID: 2915.0
Gene Symbol: GRM5
Target Organism: Homo sapiens (Human)
12.0 nM [IC50]
Target ID: P48058
Gene ID: 2893.0
Gene Symbol: GRIA4
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The mGlu5 receptor antagonists MPEP and MTEP attenuate behavioral signs of morphine withdrawal and morphine-withdrawal-induced activation of locus coeruleus neurons in rats.
2005 Feb
Effects of the mGluR5 antagonist MPEP on ethanol withdrawal induced anxiety-like syndrome in rats.
2013 Nov 26
Influence of MPEP (a selective mGluR5 antagonist) on the anticonvulsant action of novel antiepileptic drugs against maximal electroshock-induced seizures in mice.
2016 Feb 4
Conserved Hypothalamic c-Fos Activation Pattern Induced by the mGlu5 Receptor Antagonist MPEP during Peri-pubertal Development in Mice.
2016 Jul
Patents

Sample Use Guides

Male mGlu5 knockout (KO) and wild-type (WT) control mice were subjected to a forced swim test (FST) and pre-treated with either 0, 10, or 30 mg/kg of MPEP 15 minutes prior. MPEP produced a dose-dependent reduction in immobility in the FST after acute administration. Statistically significant reductions in the duration of immobility were detected at a dose of 30 mg/kg. The maximal reduction of immobility produced by MPEP was comparable with that produced by 15 mg/kg imipramine. When 5 mg/kg MPEP was administered daily for five consecutive days and tested for activity in the FST after dosing on day 5, MPEP significantly reduced immobility as with acute dosing
Route of Administration: Intraperitoneal
Rat cortical neuronal cells cultured in 96-well plates at 7–8 DIV were pretreated for 30 min with 0.2–200 μm of the mGluR5 antagonists MPEP, with or without MK801 following the addition of 150 μm Na-glutamate or 50 μm NMDA. After 24 h of incubation with drugs, cell viability was tested by measuring LDH release, using a CytoTox 96 non-radioactive cytotoxicity assay kit. LDH release based cell viability assay revealed significant neuroprotective effects of MPEP both in glutamate- and NMDA-treated cultures. Neuroprotection was observed at concentrations of 20 micro-M MPEP and above.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:58:38 GMT 2023
Edited
by admin
on Sat Dec 16 09:58:38 GMT 2023
Record UNII
AU9X845ZWM
Record Status Validated (UNII)
Record Version
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Name Type Language
2-METHYL-6-(PHENYLETHYNYL)PYRIDINE HYDROCHLORIDE
Systematic Name English
MPEP HYDROCHLORIDE
Common Name English
PYRIDINE, 2-METHYL-6-(2-PHENYLETHYNYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
PYRIDINE, 2-METHYL-6-(PHENYLETHYNYL)-, HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
CHEBI
64158
Created by admin on Sat Dec 16 09:58:38 GMT 2023 , Edited by admin on Sat Dec 16 09:58:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID9043982
Created by admin on Sat Dec 16 09:58:38 GMT 2023 , Edited by admin on Sat Dec 16 09:58:38 GMT 2023
PRIMARY
FDA UNII
AU9X845ZWM
Created by admin on Sat Dec 16 09:58:38 GMT 2023 , Edited by admin on Sat Dec 16 09:58:38 GMT 2023
PRIMARY
PUBCHEM
9794588
Created by admin on Sat Dec 16 09:58:38 GMT 2023 , Edited by admin on Sat Dec 16 09:58:38 GMT 2023
PRIMARY
CAS
219911-35-0
Created by admin on Sat Dec 16 09:58:38 GMT 2023 , Edited by admin on Sat Dec 16 09:58:38 GMT 2023
PRIMARY
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