2-Methyl-6-(phenylethynyl)pyridine

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2-Methyl-6-(phenylethynyl)pyridine
Methylphenylethynylpyridine.png
Systematic (IUPAC) name
2-Methyl-6-(phenylethynyl)pyridine
Identifiers
CAS Number 96206-92-7 N
PubChem CID: 3025961
IUPHAR/BPS 1426
ChemSpider 7970355 YesY
UNII 7VC0YVI27Y N
Chemical data
Formula C14H11N
Molecular mass 193.243 g/mol
  • CC1=CC=CC(=N1)C#CC2=CC=CC=C2
  • 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 YesY
  • Key:PKDHDJBNEKXCBI-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

2-Methyl-6-(phenylethynyl)pyridine (MPEP) is a research drug which was one of the first compounds found to act as a selective antagonist for the metabotropic glutamate receptor subtype mGluR5. After being originally patented as a liquid crystal for LCDs, it was developed by the pharmaceutical company Novartis in the late 1990s.[1] It was found to produce neuroprotective effects following acute brain injury in animal studies, although it was unclear whether these results were purely from mGluR5 blockade as it also acts as a weak NMDA antagonist,[2][3] and as a positive allosteric modulator of another subtype mGlu4,[4] and there is also evidence for a functional interaction between mGluR5 and NMDA receptors in the same populations of neurons.[5] It was also shown to produce antidepressant[6][7][8] and anxiolytic effects in animals,[9][10][11] and to reduce the effects of morphine withdrawal,[12] most likely due to direct interaction between mGluR5 and the μ-opioid receptor.[13]

The main significance of MPEP has been as a lead compound to develop more potent and selective mGluR5 antagonists such as MTEP,[14] but research using MPEP itself continues, and recently it was shown to reduce self-administration of nicotine,[15][16] cocaine,[17][18] ketamine and heroin in animals,[19] possibly through an MPEP-induced potentiation of the rewarding effect of the self-administered drug,[20] and MPEP was also shown to possess weak reinforcing effects by itself.[21]

References

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