MTEP

Short description: Chemical compound

MTEP

Identifiers

IUPAC name

* 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine

CAS Number|

* 329205-68-7 Y

PubChem CID|

* 9794218

IUPHAR/BPS|

* 3336

ChemSpider|

* 7969985 N

Chemical and physical data
Formula| C11H8N2S
Molar mass| 200.26 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CC1=NC(=CS1)C#CC2=CN=CC=C2

InChI

* InChI=1S/C11H8N2S/c1-9-13-11(8-14-9)5-4-10-3-2-6-12-7-10/h2-3,6-8H,1H3 N

* Key:NRBNGHCYDWUVLC-UHFFFAOYSA-N N

NY (what is this?) (verify)

3-((2-Methyl-4-thiazolyl)ethynyl)pyridine (MTEP) is a research drug that was developed by Merck & Co. as a selective allosteric antagonist of the metabotropic glutamate receptor subtype mGluR5. Identified through structure-activity relationship studies on an older mGluR5 antagonist MPEP,[1] MTEP has subsequently itself acted as a lead compound for newer and even more improved drugs.[2][3]

MTEP is both more potent and more selective than MPEP as a mGluR5 antagonist,[4] and produces similar neuroprotective,[5][6][7] antidepressant,[8][9][10][11] analgesic,[12][13] and anxiolytic effects but with either similar or higher efficacy depending on the test used.[14][15][16][17]

MTEP also has similar efficacy to MPEP in reducing the symptoms of morphine withdrawal,[18][19][20] and has anti-addictive effects in a variety of animal models, both reducing ethanol self-administration,[21][22][23][24] and also decreasing the addictive effects of nicotine, cocaine and methamphetamine.[25][26][27][28][29]

## See also

* MPEP
* MFZ 10-7
* Fenobam

## References

1. ↑ "3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]-pyridine: a potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity". Journal of Medicinal Chemistry 46 (2): 204–206. January 2003. doi:10.1021/jm025570j. PMID 12519057.
2. ↑ "Synthesis and structure-activity relationships of 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine analogues as potent, noncompetitive metabotropic glutamate receptor subtype 5 antagonists; search for cocaine medications". Journal of Medicinal Chemistry 49 (3): 1080–1100. February 2006. doi:10.1021/jm050570f. PMID 16451073.
3. ↑ "Discovery of heterobicyclic templates for novel metabotropic glutamate receptor subtype 5 antagonists". Bioorganic & Medicinal Chemistry Letters 17 (11): 2987–2991. June 2007. doi:10.1016/j.bmcl.2007.03.066. PMID 17446071.
4. ↑ "Metabotropic glutamate receptor subtype 5 antagonists MPEP and MTEP". CNS Drug Reviews 12 (2): 149–166. 2006. doi:10.1111/j.1527-3458.2006.00149.x. PMID 16958988.
5. ↑ "Neuroprotective activity of the mGluR5 antagonists MPEP and MTEP against acute excitotoxicity differs and does not reflect actions at mGluR5 receptors". British Journal of Pharmacology 145 (4): 527–534. June 2005. doi:10.1038/sj.bjp.0706219. PMID 15821750.
6. ↑ "Neuroprotective effects of MTEP, a selective mGluR5 antagonists and neuropeptide Y on the kainate-induced toxicity in primary neuronal cultures". Pharmacological Reports 58 (6): 846–858. 2006. PMID 17220542.
7. ↑ "Neuroprotective activity of selective mGlu1 and mGlu5 antagonists in vitro and in vivo". European Journal of Pharmacology 554 (1): 18–29. January 2007. doi:10.1016/j.ejphar.2006.09.061. PMID 17109843.
8. ↑ "Potential antidepressant-like effect of MTEP, a potent and highly selective mGluR5 antagonist". Pharmacology, Biochemistry, and Behavior 81 (4): 901–906. August 2005. doi:10.1016/j.pbb.2005.06.015. PMID 16040106.
9. ↑ "Antidepressant-like and anxiolytic-like actions of the mGlu5 receptor antagonist MTEP, microinjected into lateral septal nuclei of male Wistar rats". Progress in Neuro-Psychopharmacology & Biological Psychiatry 30 (6): 1129–1135. August 2006. doi:10.1016/j.pnpbp.2006.04.022. PMID 16759778.
10. ↑ "Metabotropic glutamate 5 receptor antagonism is associated with antidepressant-like effects in mice". The Journal of Pharmacology and Experimental Therapeutics 319 (1): 254–259. October 2006. doi:10.1124/jpet.106.103143. PMID 16803860.
11. ↑ "Antidepressant-like effects of mGluR1 and mGluR5 antagonists in the rat forced swim and the mouse tail suspension tests". European Neuropsychopharmacology 17 (3): 172–179. February 2007. doi:10.1016/j.euroneuro.2006.03.002. PMID 16630709.
12. ↑ "Assessing the role of metabotropic glutamate receptor 5 in multiple nociceptive modalities". European Journal of Pharmacology 506 (2): 107–118. December 2004. doi:10.1016/j.ejphar.2004.11.005. PMID 15588730.
13. ↑ "The antinociceptive and anxiolytic-like effects of the metabotropic glutamate receptor 5 (mGluR5) antagonists, MPEP and MTEP, and the mGluR1 antagonist, LY456236, in rodents: a comparison of efficacy and side-effect profiles". Psychopharmacology 179 (1): 207–217. April 2005. doi:10.1007/s00213-005-2143-4. PMID 15682298.
14. ↑ "Anxiolytic-like effects of MTEP, a potent and selective mGlu5 receptor agonist does not involve GABA(A) signaling". Neuropharmacology 47 (3): 342–350. September 2004. doi:10.1016/j.neuropharm.2004.04.013. PMID 15275823.
15. ↑ "The behavioral profile of the potent and selective mGlu5 receptor antagonist 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine (MTEP) in rodent models of anxiety". Neuropsychopharmacology 29 (11): 1971–1979. November 2004. doi:10.1038/sj.npp.1300540. PMID 15305166.
16. ↑ "Anxiolytic-like effects of mGlu1 and mGlu5 receptor antagonists in rats". European Journal of Pharmacology 514 (1): 25–34. May 2005. doi:10.1016/j.ejphar.2005.03.028. PMID 15878321.
17. ↑ "Anxiolytic-like action of MTEP expressed in the conflict drinking Vogel test in rats is serotonin dependent". Neuropharmacology 53 (6): 741–748. November 2007. doi:10.1016/j.neuropharm.2007.08.002. PMID 17870136.
18. ↑ "Selective mGlu5 receptor antagonist MTEP attenuates naloxone-induced morphine withdrawal symptoms". Polish Journal of Pharmacology 56 (6): 863–866. 2004. PMID 15662102. http://www.if-pan.krakow.pl/pjp/pdf/2004/6_863.pdf.
19. ↑ "The mGlu5 receptor antagonists MPEP and MTEP attenuate behavioral signs of morphine withdrawal and morphine-withdrawal-induced activation of locus coeruleus neurons in rats". Neuropharmacology 48 (2): 173–180. February 2005. doi:10.1016/j.neuropharm.2004.09.010. PMID 15695156.
20. ↑ "Comparison of the effects of mGluR1 and mGluR5 antagonists on the expression of behavioral sensitization to the locomotor effect of morphine and the morphine withdrawal jumping in mice". European Journal of Pharmacology 558 (1–3): 113–118. March 2007. doi:10.1016/j.ejphar.2006.11.067. PMID 17222405.
21. ↑ "The metabotropic glutamate 5 receptor antagonist 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]-pyridine reduces ethanol self-administration in multiple strains of alcohol-preferring rats and regulates olfactory glutamatergic systems". The Journal of Pharmacology and Experimental Therapeutics 315 (2): 590–600. November 2005. doi:10.1124/jpet.105.090449. PMID 16014750.
22. ↑ "Assessing appetitive and consummatory phases of ethanol self-administration in C57BL/6J mice under operant conditions: regulation by mGlu5 receptor antagonism". Psychopharmacology 190 (1): 21–29. January 2007. doi:10.1007/s00213-006-0583-0. PMID 17096086.
23. ↑ "Combined antagonism of glutamate mGlu5 and adenosine A2A receptors interact to regulate alcohol-seeking in rats". The International Journal of Neuropsychopharmacology 11 (2): 229–241. March 2008. doi:10.1017/S1461145707007845. PMID 17517168.
24. ↑ "The influence of various glutamate receptors antagonists on anxiety-like effect of ethanol withdrawal in a plus-maze test in rats". European Journal of Pharmacology 598 (1–3): 57–63. November 2008. doi:10.1016/j.ejphar.2008.09.026. PMID 18838071.
25. ↑ "Effects of group I metabotropic glutamate receptor antagonists on the behavioral sensitization to motor effects of cocaine in rats". Psychopharmacology 187 (4): 397–404. September 2006. doi:10.1007/s00213-006-0440-1. PMID 16896963.
26. ↑ "Metabotropic glutamate 5 receptor (mGluR5) antagonists decrease nicotine seeking, but do not affect the reinforcement enhancing effects of nicotine". Neuropsychopharmacology 33 (9): 2139–2147. August 2008. doi:10.1038/sj.npp.1301623. PMID 18046312.
27. ↑ "mGluR5 antagonism attenuates methamphetamine reinforcement and prevents reinstatement of methamphetamine-seeking behavior in rats". Neuropsychopharmacology 34 (4): 820–833. March 2009. doi:10.1038/npp.2008.140. PMID 18800068.
28. ↑ "A role for mGluR5 receptors in intravenous methamphetamine self-administration". Annals of the New York Academy of Sciences 1139 (1): 206–211. October 2008. doi:10.1196/annals.1432.034. PMID 18991866. Bibcode: 2008NYASA1139..206O.
29. ↑ "Dissociation of the effects of MTEP [3-[(2-methyl-1,3-thiazol-4-yl)ethynylpiperidine] on conditioned reinstatement and reinforcement: comparison between cocaine and a conventional reinforcer"]. The Journal of Pharmacology and Experimental Therapeutics 329 (3): 1084–1090. June 2009. doi:10.1124/jpet.109.151357. PMID 19258516.

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*[CID]: Compound ID