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SIB-1893

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Chemical compound

Pharmaceutical compound

SIB-1893
Identifiers

IUPAC name (E)-2-methyl-6-(2-phenylethenyl)pyridine
CAS Number	7370-21-0^Y
PubChemCID	235382
ChemSpider	4470920^N
UNII	4X2F5X24UK
ChEMBL	ChEMBL88612^N
CompTox Dashboard(EPA)	DTXSID801017353
Chemical and physical data
Formula	C₁₄H₁₃N
Molar mass	195.265 g·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+^N Key:SISOFUCTXZKSOQ-ZHACJKMWSA-N^N
^NY (what is this?) (verify)

SIB-1893 is a drug used in scientific research which was one of the first compounds developed that acts as a selectiveantagonist for themetabotropic glutamate receptor subtypemGluR₅.^[1] It hasanticonvulsant andneuroprotective effects,^[2] and reduces glutamate release.^[3] It has also been found to act as a positive allosteric modulator ofmGluR₄.^[4]

^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.PMC 1573757.PMID 12684257.

mGluR₁Tooltip Metabotropic glutamate receptor 1	Agonists:ACPD DHPG Glutamate Ibotenic acid Quisqualic acid Ro01-6128 Ro67-4853 Ro67-7476 VU-71 Theanine Antagonists:BAY 36-7620 CPCCOEt Cyclothiazide LY-367,385 LY-456,236 MCPG NPS-2390
mGluR₅Tooltip Metabotropic glutamate receptor 5	Agonists:ACPD ADX-47273 CDPPB CHPG DFB DHPG Glutamate Ibotenic acid Quisqualic acid VU-1545;Positive allosteric modulators:LSN2463359 Antagonists:CTEP DMeOB LY-344,545 Mavoglurant MCPG NPS-2390 Remeglurant SIB-1757 SIB-1893;Negative allosteric modulators:AZD9272 Basimglurant Dipraglurant Fenobam GRN-529 MPEP MTEP Raseglurant

mGluR₂Tooltip Metabotropic glutamate receptor 2

mGluR₃Tooltip Metabotropic glutamate receptor 3

mGluR₄Tooltip Metabotropic glutamate receptor 4	Agonists:Glutamate L-AP4 LSP2-9166 PHCCC VU-001,171 VU-0155,041;Positive allosteric modulators:Foliglurax MPEP Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₆Tooltip Metabotropic glutamate receptor 6	Agonists:Glutamate L-AP4 Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₇Tooltip Metabotropic glutamate receptor 7	Agonists:AMN082 Glutamate L-AP4 LSP2-9166 Antagonists:CPPG MAP4 MMPIP MPPG MSOP MTPG UBP-1112 XAP044;Negative allosteric modulators:ADX71743
mGluR₈Tooltip Metabotropic glutamate receptor 8	Agonists:DCPG Glutamate L-AP4;Positive allosteric modulators:AZ12216052 Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112

See also:Receptor/signaling modulators •Ionotropic glutamate receptor modulators •Glutamate metabolism/transport modulators

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