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{{Short description|Chemical compound}}
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{{Hatnote|MTEP also stands for [[Magnetothermoelectric Power]], for the [[Medium Term Economic Program]], for the [[Medium-Term Employment Plan]], for the OECD's [[Medium-Term Expenditure Programme]], for the [[MISO Transmission Expansion Plan|MISO (Midwest Independent System Operator) Transmission Expansion Plan]], for the [[Multinational Test and Evaluation Program]], and for the [[Myanmar Total Exploration and Production]] Company}}
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{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424696647
| IUPAC_name = 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine
| image = Mtep.png
| alt = Skeletal formula
| width = 200
| image2 = MTEP-3D-spacefill.png
| alt2 = Space-filling model
 
<!--Clinical data-->
Line 16 ⟶ 24:
 
<!--Identifiers-->
| IUPHAR_ligand = 3336
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 329205-68-7
| PubChem = 9794218
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7969985
 
<!--Chemical data-->
| C=11 | H=8 | N=2 | S=1
| molecular_weight = 200.260 g/mol
| smiles = CC1=NC(=CS1)C#CC2=CN=CC=C2
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C11H8N2S/c1-9-13-11(8-14-9)5-4-10-3-2-6-12-7-10/h2-3,6-8H,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NRBNGHCYDWUVLC-UHFFFAOYSA-N
}}
 
'''3-((2-Methyl-4-thiazolyl)ethynyl)pyridine''' ('''MTEP''') is a research drug that was developed by [[Merck & Co.]] as a selective [[allosteric]] [[Antagonist (pharmacology)|antagonist]] of the [[metabotropic glutamate receptor]] subtype [[Metabotropic glutamate receptor 5|mGluR5]]. Identified through [[structure-activity relationship]] studies on an older mGluR5 antagonist [[2-Methyl-6-(phenylethynyl)pyridine|MPEP]],<ref>{{cite journal |author vauthors = Cosford ND, Tehrani L, Roppe J, ''etSchweiger al.''E, Smith ND, Anderson J, Bristow L, Brodkin J, Jiang X, McDonald I, Rao S, Washburn M, Varney MA | display-authors = 6 | title = 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 =J. Med.Journal Chem.of Medicinal Chemistry | volume = 46 | issue = 2 | pages=204–6 |year=2003 204–206 |month date = January 2003 | pmid = 12519057 | doi = 10.1021/jm025570j |url=}}</ref> MTEP has subsequently itself acted as a [[lead compound]] for newer and even more improved drugs.<ref>{{cite journal |author vauthors = Iso Y, Grajkowska E, Wroblewski JT, ''etDavis al.''J, Goeders NE, Johnson KM, Sanker S, Roth BL, Tueckmantel W, Kozikowski AP | display-authors = 6 | title = 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 =J. Med.Journal Chem.of Medicinal Chemistry | volume = 49 | issue = 3 | pages=1080–100 |year=2006 1080–1100 |month date = February 2006 | pmid = 16451073 | doi = 10.1021/jm050570f |url=}}</ref><ref>{{cite journal |author vauthors = Kulkarni SS, Newman AH | title = Discovery of heterobicyclic templates for novel metabotropic glutamate receptor subtype 5 antagonists | journal =Bioorg. Med.Bioorganic Chem.& Lett.Medicinal Chemistry Letters | volume = 17 | issue = 11 | pages=2987–91 |year=2007 2987–2991 |month date = June 2007 | pmid = 17446071 | pmc = 1973162 | doi = 10.1016/j.bmcl.2007.03.066 |url=}}</ref>
 
MTEP is both more [[Potency (pharmacology)|potent]] and more [[Functional selectivity|selective]] than [[2-Methyl-6-(phenylethynyl)pyridine|MPEP]] as a mGluR5 antagonist,<ref>{{cite journal | vauthors = Lea PM, Faden AI | title = Metabotropic glutamate receptor subtype 5 antagonists MPEP and MTEP | journal = CNS Drug Reviews | volume = 12 | issue = 2 | pages = 149–166 | year = 2006 | pmid = 16958988 | pmc = 6494124 | doi = 10.1111/j.1527-3458.2006.00149.x }}</ref> and produces similar [[neuroprotective]],<ref>{{cite journal | vauthors = Lea PM, Movsesyan VA, Faden AI | title = Neuroprotective activity of the mGluR5 antagonists MPEP and MTEP against acute excitotoxicity differs and does not reflect actions at mGluR5 receptors | journal = British Journal of Pharmacology | volume = 145 | issue = 4 | pages = 527–534 | date = June 2005 | pmid = 15821750 | pmc = 1576169 | doi = 10.1038/sj.bjp.0706219 }}</ref><ref>{{cite journal | vauthors = Domin H, Kajta M, Smiałowska M | title = Neuroprotective effects of MTEP, a selective mGluR5 antagonists and neuropeptide Y on the kainate-induced toxicity in primary neuronal cultures | journal = Pharmacological Reports | volume = 58 | issue = 6 | pages = 846–858 | year = 2006 | pmid = 17220542 }}</ref><ref>{{cite journal | vauthors = Szydlowska K, Kaminska B, Baude A, Parsons CG, Danysz W | title = Neuroprotective activity of selective mGlu1 and mGlu5 antagonists in vitro and in vivo | journal = European Journal of Pharmacology | volume = 554 | issue = 1 | pages = 18–29 | date = January 2007 | pmid = 17109843 | doi = 10.1016/j.ejphar.2006.09.061 }}</ref> [[antidepressant]],<ref>{{cite journal | vauthors = Pałucha A, Brański P, Szewczyk B, Wierońska JM, Kłak K, Pilc A | title = Potential antidepressant-like effect of MTEP, a potent and highly selective mGluR5 antagonist | journal = Pharmacology, Biochemistry, and Behavior | volume = 81 | issue = 4 | pages = 901–906 | date = August 2005 | pmid = 16040106 | doi = 10.1016/j.pbb.2005.06.015 | s2cid = 42920507 }}</ref><ref>{{cite journal | vauthors = Molina-Hernández M, Tellez-Alcántara NP, Pérez-García J, Olivera-Lopez JI, Jaramillo MT | title = Antidepressant-like and anxiolytic-like actions of the mGlu5 receptor antagonist MTEP, microinjected into lateral septal nuclei of male Wistar rats | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 30 | issue = 6 | pages = 1129–1135 | date = August 2006 | pmid = 16759778 | doi = 10.1016/j.pnpbp.2006.04.022 | s2cid = 45937198 }}</ref><ref>{{cite journal | vauthors = Li X, Need AB, Baez M, Witkin JM | title = Metabotropic glutamate 5 receptor antagonism is associated with antidepressant-like effects in mice | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 319 | issue = 1 | pages = 254–259 | date = October 2006 | pmid = 16803860 | doi = 10.1124/jpet.106.103143 | s2cid = 14632318 }}</ref><ref>{{cite journal | vauthors = Belozertseva IV, Kos T, Popik P, Danysz W, Bespalov AY | title = Antidepressant-like effects of mGluR1 and mGluR5 antagonists in the rat forced swim and the mouse tail suspension tests | journal = European Neuropsychopharmacology | volume = 17 | issue = 3 | pages = 172–179 | date = February 2007 | pmid = 16630709 | doi = 10.1016/j.euroneuro.2006.03.002 | s2cid = 2420850 }}</ref> [[analgesic]],<ref>{{cite journal | vauthors = Zhu CZ, Wilson SG, Mikusa JP, Wismer CT, Gauvin DM, Lynch JJ, Wade CL, Decker MW, Honore P | display-authors = 6 | title = Assessing the role of metabotropic glutamate receptor 5 in multiple nociceptive modalities | journal = European Journal of Pharmacology | volume = 506 | issue = 2 | pages = 107–118 | date = December 2004 | pmid = 15588730 | doi = 10.1016/j.ejphar.2004.11.005 }}</ref><ref>{{cite journal | vauthors = Varty GB, Grilli M, Forlani A, Fredduzzi S, Grzelak ME, Guthrie DH, Hodgson RA, Lu SX, Nicolussi E, Pond AJ, Parker EM, Hunter JC, Higgins GA, Reggiani A, Bertorelli R | display-authors = 6 | title = 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 | journal = Psychopharmacology | volume = 179 | issue = 1 | pages = 207–217 | date = April 2005 | pmid = 15682298 | doi = 10.1007/s00213-005-2143-4 | s2cid = 21807900 }}</ref> and [[anxiolytic]] effects but with either similar or higher [[efficacy]] depending on the test used.<ref>{{cite journal | vauthors = Klodzinska A, Tatarczyńska E, Chojnacka-Wójcik E, Nowak G, Cosford ND, Pilc A | title = Anxiolytic-like effects of MTEP, a potent and selective mGlu5 receptor agonist does not involve GABA(A) signaling | journal = Neuropharmacology | volume = 47 | issue = 3 | pages = 342–350 | date = September 2004 | pmid = 15275823 | doi = 10.1016/j.neuropharm.2004.04.013 | s2cid = 54432014 }}</ref><ref>{{cite journal | vauthors = Busse CS, Brodkin J, Tattersall D, Anderson JJ, Warren N, Tehrani L, Bristow LJ, Varney MA, Cosford ND | display-authors = 6 | title = 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 | journal = Neuropsychopharmacology | volume = 29 | issue = 11 | pages = 1971–1979 | date = November 2004 | pmid = 15305166 | doi = 10.1038/sj.npp.1300540 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Pietraszek M, Sukhanov I, Maciejak P, Szyndler J, Gravius A, Wisłowska A, Płaźnik A, Bespalov AY, Danysz W | display-authors = 6 | title = Anxiolytic-like effects of mGlu1 and mGlu5 receptor antagonists in rats | journal = European Journal of Pharmacology | volume = 514 | issue = 1 | pages = 25–34 | date = May 2005 | pmid = 15878321 | doi = 10.1016/j.ejphar.2005.03.028 }}</ref><ref>{{cite journal | vauthors = Stachowicz K, Gołembiowska K, Sowa M, Nowak G, Chojnacka-Wójcik E, Pilc A | title = Anxiolytic-like action of MTEP expressed in the conflict drinking Vogel test in rats is serotonin dependent | journal = Neuropharmacology | volume = 53 | issue = 6 | pages = 741–748 | date = November 2007 | pmid = 17870136 | doi = 10.1016/j.neuropharm.2007.08.002 | s2cid = 24833690 }}</ref>
MTEP is both more [[Potency (pharmacology)|potent]] and more [[Functional selectivity|selective]] than MPEP as a mGluR5 antagonist,<ref>{{cite DOI|10.1111/j.1527-3458.2006.00149.x}}</ref> and produces similar [[neuroprotective]],<ref>{{cite DOI|10.1038/sj.bjp.0706219}}</ref><ref>{{cite PMID|17220542}}</ref><ref>{{cite DOI|10.1016/j.ejphar.2006.09.061}}</ref> [[antidepressant]],<ref>{{cite DOI|10.1016/j.pbb.2005.06.015}}</ref><ref>{{cite DOI|10.1016/j.pnpbp.2006.04.022}}</ref><ref>{{cite DOI|10.1124/jpet.106.103143}}</ref><ref>{{cite DOI|10.1016/j.euroneuro.2006.03.002}}</ref> [[analgesic]],<ref>{{cite DOI|10.1016/j.ejphar.2004.11.005}}</ref><ref>{{cite DOI|10.1007/s00213-005-2143-4}}</ref> and [[anxiolytic]] effects but with either similar or higher [[efficacy]] depending on the test used.<ref>{{cite DOI|10.1016/j.neuropharm.2004.04.013}}</ref><ref>{{cite DOI|10.1038/sj.npp.1300540}}</ref><ref>{{cite DOI|10.1016/j.ejphar.2005.03.028 |url=}}</ref><ref>{{cite DOI|10.1016/j.neuropharm.2007.08.002}}</ref>
 
MTEP also has similar efficacy to MPEP in reducing the symptoms of [[morphine]] [[Drug withdrawal|withdrawal]],<ref>{{cite journal |author vauthors = Pałucha A, Brański P, Pilc A | title = Selective mGlu5 receptor antagonist MTEP attenuates naloxone-induced morphine with-drawalwithdrawal symptoms | journal =Pol JPolish PharmacolJournal of Pharmacology | volume = 56 | issue = 6 | pages =863–6 863–866 | year = 2004 | pmid = 15662102 |doi= |url = http://www.if-pan.krakow.pl/pjp/pdf/2004/6_863.pdf }}</ref><ref>{{cite journal |author vauthors = Rasmussen K, Martin H, Berger JE, Seager MA | title = The mGlu5 receptor antagonists MPEP and MTEP attenuate behavioral signs of morphine withdrawal and morphine-withdrawal-induced activation of locus coeruleus neurons in rats | journal = Neuropharmacology | volume = 48 | issue = 2 | pages=173–80 |year=2005 173–180 |month date = February 2005 | pmid = 15695156 | doi = 10.1016/j.neuropharm.2004.09.010 |url s2cid = 13552709 }}</ref><ref>{{cite journal |author vauthors = Kotlinska J, Bochenski M | title = 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 | journal =Eur. J.European Pharmacol.Journal of Pharmacology | volume = 558 | issue =1-3 1–3 | pages=113–8 |year=2007 113–118 |month date = March 2007 | pmid = 17222405 | doi = 10.1016/j.ejphar.2006.11.067 |url=}}</ref> and has anti-addictive effects in a variety of animal models, both reducing ethanol self-administration,<ref>{{cite journal |author vauthors = Cowen MS, Djouma E, Lawrence AJ | title = 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 | journal =J. Pharmacol.The Exp.Journal Ther.of Pharmacology and Experimental Therapeutics | volume = 315 | issue = 2 | pages = 590–600 |year=2005 |monthdate = November 2005 | pmid = 16014750 | doi = 10.1124/jpet.105.090449 |url s2cid = 11501029 }}</ref><ref>{{cite journal |author vauthors = Cowen MS, Krstew E, Lawrence AJ | title = Assessing appetitive and consummatory phases of ethanol self-administration in C57BL/6J mice under operant conditions: regulation by mGlu5 receptor antagonism | journal = Psychopharmacology (Berl.) | volume = 190 | issue = 1 | pages=21–9 |year=2007 21–29 |month date = January 2007 | pmid = 17096086 | doi = 10.1007/s00213-006-0583-0 |url s2cid = 19977179 }}</ref><ref>{{cite journal |author vauthors = Adams CL, Cowen MS, Short JL, Lawrence AJ | title = Combined antagonism of glutamate mGlu5 and adenosine A2A receptors interact to regulate alcohol-seeking in rats | journal =Int. J.The Neuropsychopharmacol.International Journal of Neuropsychopharmacology | volume = 11 | issue = 2 | pages=229–41 |year=2008 229–241 |month date = March 2008 | pmid = 17517168 | doi = 10.1017/S1461145707007845 |url doi-access = free | hdl = 11343/32923 | hdl-access = free }}</ref><ref>{{cite journal |author vauthors = Kotlinska J, Bochenski M | title = The influence of various glutamate receptors antagonists on anxiety-like effect of ethanol withdrawal in a plus-maze test in rats | journal =Eur. J.European Pharmacol.Journal of Pharmacology | volume = 598 | issue =1-3 1–3 | pages = 57–63 |year=2008 |monthdate = November 2008 | pmid = 18838071 | doi = 10.1016/j.ejphar.2008.09.026 |url=}}</ref> and also decreasing the addictive effects of [[nicotine]], [[cocaine]] and [[methamphetamine]].<ref>{{cite journal |author vauthors = Dravolina OA, Danysz W, Bespalov AY | title = Effects of group I metabotropic glutamate receptor antagonists on the behavioral sensitization to motor effects of cocaine in rats | journal = Psychopharmacology (Berl.) | volume = 187 | issue = 4 | pages = 397–404 |year=2006 |monthdate = September 2006 | pmid = 16896963 | doi = 10.1007/s00213-006-0440-1 |url s2cid = 21231365 }}</ref><ref>{{cite journal |author vauthors = Palmatier MI, Liu X, Donny EC, Caggiula AR, Sved AF | title = Metabotropic glutamate 5 receptor (mGluR5) antagonists decrease nicotine seeking, but do not affect the reinforcement enhancing effects of nicotine | journal = Neuropsychopharmacology | volume = 33 | issue = 9 | pages=2139–47 |year=2008 2139–2147 |month date = August 2008 | pmid = 18046312 | pmc = 2812904 | doi = 10.1038/sj.npp.1301623 |url=}}</ref><ref>{{cite journal |author vauthors = Gass JT, Osborne MP, Watson NL, Brown JL, Olive MF | title = mGluR5 antagonism attenuates methamphetamine reinforcement and prevents reinstatement of methamphetamine-seeking behavior in rats | journal = Neuropsychopharmacology | volume = 34 | issue = 4 | pages=820–33 |year=2009 820–833 |month date = March 2009 | pmid = 18800068 | pmc = 2669746 | doi = 10.1038/npp.2008.140 |url=}}</ref><ref>{{cite journal |author vauthors = Osborne MP, Olive MF | title = A role for mGluR5 receptors in intravenous methamphetamine self-administration | journal =Ann. N.Annals Y.of Acad.the Sci.New York Academy of Sciences | volume = 1139 | issue = 1 | pages=206–11 |year=2008 206–211 |month date = October 2008 | pmid = 18991866 | doi = 10.1196/annals.1432.034 |url s2cid = 207012906 | bibcode = 2008NYASA1139..206O }}</ref><ref>{{cite journal |author vauthors = Martin-Fardon R, Baptista MA, Dayas CV, Weiss F | title = Dissociation of the effects of MTEP [3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]piperidine] on conditioned reinstatement and reinforcement: comparison between cocaine and a conventional reinforcer | journal =J. Pharmacol.The Exp.Journal Ther.of Pharmacology and Experimental Therapeutics | volume = 329 | issue = 3 | pages=1084–90 |year=2009 1084–1090 |month date = June 2009 | pmid = 19258516 | pmc = 2683783 | doi = 10.1124/jpet.109.151357 |url=}}</ref>
 
==References See also ==
*[[2-Methyl-6-(phenylethynyl)pyridine|MPEP]]
{{Reflist|2}}▼
*[[MFZ 10-7]]
{{Glutamate_receptor_ligands}}
*[[Fenobam]]
 
== References ==
[[Category:Receptor antagonists]]▼
▲{{Reflist|230em}}
[[Category:Thiazoles]]▼
[[Category:Pyridines]]▼
[[Category:Alkynes]]▼
 
{{Metabotropic glutamate receptor modulators}}
[[sr:MTEP]]
 
▲[[Category:Thiazoles]]
▲[[Category:Alkynes3-Pyridyl compounds]]
▲[[Category:PyridinesAlkyne derivatives]]
▲[[Category:ReceptorMGlu5 receptor antagonists]]
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