SIB-1893

SIB-1893
Identifiers
	IUPAC name (E)-2-methyl-6-(2-phenylethenyl)pyridine;
CAS Number	7370-21-0;
PubChemCID	235382;
ChemSpider	4470920;
UNII	4X2F5X24UK;
ChEMBL	ChEMBL88612;
CompTox Dashboard(EPA)	DTXSID801017353;
Chemical and physical data
Formula	C14H13N
Molar mass	195.265g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccccc1\C=C\c(nc2C)ccc2;
	InChI InChI=1S/C14H13N/c1-12-6-5-9-14(15-12)11-10-13-7-3-2-4-8-13/h2-11H,1H3/b11-10+; Key:SISOFUCTXZKSOQ-ZHACJKMWSA-N;
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SIB-1893is a drug used in scientific research which was one of the first compounds developed that acts as a selectiveantagonistfor themetabotropic glutamate receptorsubtypemGluR₅.^[1]It hasanticonvulsantandneuroprotectiveeffects,^[2]and reduces glutamate release.^[3]It has also been found to act as a positive allosteric modulator ofmGluR₄.^[4]

References

^Varney MA, Cosford ND, Jachec C, Rao SP, Sacaan A, Lin FF, Bleicher L, Santori EM, Flor PJ, Allgeier H, Gasparini F, Kuhn R, Hess SD, Veliçelebi G, Johnson EC (July 1999). "SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5".The Journal of Pharmacology and Experimental Therapeutics.290(1): 170–81.PMID 10381773.
^Chapman AG, Nanan K, Williams M, Meldrum BS (July 2000). "Anticonvulsant activity of two metabotropic glutamate group I antagonists selective for the mGlu5 receptor: 2-methyl-6-(phenylethynyl)-pyridine (MPEP), and (E)-6-methyl-2-styryl-pyridine (SIB 1893)".Neuropharmacology.39(9): 1567–74.doi:10.1016/S0028-3908(99)00242-7.PMID 10854901.S2CID 21528282.
^Wang SJ, Sihra TS (June 2004). "Noncompetitive metabotropic glutamate5 receptor antagonist (E)-2-methyl-6-styryl-pyridine (SIB1893) depresses glutamate release through inhibition of voltage-dependent Ca2+ entry in rat cerebrocortical nerve terminals (synaptosomes)".The Journal of Pharmacology and Experimental Therapeutics.309(3): 951–8.doi:10.1124/jpet.103.064881.PMID 14982967.S2CID 800526.
^Mathiesen JM, Svendsen N, Bräuner-Osborne H, Thomsen C, Ramirez MT (March 2003)."Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP".British Journal of Pharmacology.138(6): 1026–30.doi:10.1038/sj.bjp.0705159.PMC1573757.PMID 12684257.

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