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MedKoo Cat#: 532701 | Name: SIB-1893
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SIB-1893 is a highly selective non-competitive antagonist for the metabotropic glutamate mGlu5 receptor subtype; displays an IC50 value of 0.3 μM at hmGlu5, compared with > 100 μM at hmGlu1b, hmGlu2, hmGlu6, hmGlu7 and hmGlu8. It positive allosteric modulator at mGlu4 receptors.

Chemical Structure

SIB-1893
SIB-1893
CAS#7370-21-0

Theoretical Analysis

MedKoo Cat#: 532701

Name: SIB-1893

CAS#: 7370-21-0

Chemical Formula: C14H13N

Exact Mass: 195.1048

Molecular Weight: 195.27

Elemental Analysis: C, 86.12; H, 6.71; N, 7.17

Price and Availability

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10mg USD 475.00 2 weeks
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Related CAS #
No Data
Synonym
SIB-1893; SIB 1893; SIB1893.
IUPAC/Chemical Name
2-Methyl-6-(2-phenylethenyl)pyridine
InChi Key
SISOFUCTXZKSOQ-ZHACJKMWSA-N
InChi Code
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+
SMILES Code
CC1=NC(/C=C/C2=CC=CC=C2)=CC=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
SIB-1893 displays an IC50 value of 0.3 μM at hmGlu5, compared with > 100 μM at hmGlu1b, hmGlu2, hmGlu6, hmGlu7 and hmGlu8.
In vitro activity:
SIB-1893 acts as a positive allosteric modulator for hmGluR4, enhancing the efficacy of L-AP4 in guanosine 5'-O-(3-[(35)S]thiotriphosphate binding and cAMP studies. SIB-1893's effects were receptor-specific, dependent on activation, and fully blocked by the mGluR4 antagonist (RS)-alpha-cyclopropyl-4-phosphonophenylglycine (CPPG). SIB-1893 caused a two-fold decrease in K(D) in [(3)H]L-AP4 binding without affecting B(max). Reference: Br J Pharmacol. 2003 Mar;138(6):1026-30. https://pubmed.ncbi.nlm.nih.gov/12684257/
In vivo activity:
SIB-1893, a non-competitive antagonist of metabotropic glutamate receptor subtype 5, showed no impact on pentetrazole-induced convulsions in mice at doses from 0.25 to 10 mg/kg. It did not alter the protective effects of various antiepileptic drugs, and the combined treatment with these drugs did not cause motor impairment, except for phenobarbital, which led to long-term memory disturbances. Reference: Pol J Pharmacol. 2003 Sep-Oct;55(5):735-40. https://pubmed.ncbi.nlm.nih.gov/14704469/

Preparing Stock Solutions

The following data is based on the product molecular weight 195.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Mathiesen JM, Svendsen N, Bräuner-Osborne H, Thomsen C, Ramirez MT. Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP. Br J Pharmacol. 2003 Mar;138(6):1026-30. doi: 10.1038/sj.bjp.0705159. PMID: 12684257; PMCID: PMC1573757. 2. 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. SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5. J Pharmacol Exp Ther. 1999 Jul;290(1):170-81. PMID: 10381773. 3. Borowicz KK, Piskorska B, Łuszczki J, Czuczwar SJ. Influence of SIB 1893, a selective mGluR5 receptor antagonist, on the anticonvulsant activity of conventional antiepileptic drugs in two models of experimental epilepsy. Pol J Pharmacol. 2003 Sep-Oct;55(5):735-40. PMID: 14704469. 4. Luszczki J, Borowicz KK, Czuczwar SJ. Sib 1893 possesses pro- and anticonvulsant activity in the electroshock seizure threshold test in mice. Pol J Pharmacol. 2002 Sep-Oct;54(5):517-20. PMID: 12593540.
In vitro protocol:
1. Mathiesen JM, Svendsen N, Bräuner-Osborne H, Thomsen C, Ramirez MT. Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP. Br J Pharmacol. 2003 Mar;138(6):1026-30. doi: 10.1038/sj.bjp.0705159. PMID: 12684257; PMCID: PMC1573757. 2. 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. SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5. J Pharmacol Exp Ther. 1999 Jul;290(1):170-81. PMID: 10381773.
In vivo protocol:
1. Borowicz KK, Piskorska B, Łuszczki J, Czuczwar SJ. Influence of SIB 1893, a selective mGluR5 receptor antagonist, on the anticonvulsant activity of conventional antiepileptic drugs in two models of experimental epilepsy. Pol J Pharmacol. 2003 Sep-Oct;55(5):735-40. PMID: 14704469. 2. Luszczki J, Borowicz KK, Czuczwar SJ. Sib 1893 possesses pro- and anticonvulsant activity in the electroshock seizure threshold test in mice. Pol J Pharmacol. 2002 Sep-Oct;54(5):517-20. PMID: 12593540.
1: Łuszczki JJ, Borowicz KK, Czuczwar SJ. Non-competitive metabotropic glutamate subtype 5 receptor antagonist (SIB-1893) decreases body temperature in rats. Pharmacol Rep. 2005 Nov-Dec;57(6):795-801. PubMed PMID: 16382199. 2: Borowicz KK, Łuszczki JJ, Czuczwar SJ. SIB 1893, a selective mGluR5 receptor antagonist, potentiates the anticonvulsant activity of oxcarbazepine against amygdala-kindled convulsions in rats. Pol J Pharmacol. 2004 Jul-Aug;56(4):459-64. PubMed PMID: 15520501. 3: Borowicz KK, Piskorska B, Łuszczki J, Czuczwar SJ. Influence of SIB 1893, a selective mGluR5 receptor antagonist, on the anticonvulsant activity of conventional antiepileptic drugs in two models of experimental epilepsy. Pol J Pharmacol. 2003 Sep-Oct;55(5):735-40. PubMed PMID: 14704469. 4: Mathiesen JM, Svendsen N, Bräuner-Osborne H, Thomsen C, Ramirez MT. Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP. Br J Pharmacol. 2003 Mar;138(6):1026-30. PubMed PMID: 12684257; PubMed Central PMCID: PMC1573757. 5: Luszczki J, Borowicz KK, Czuczwar SJ. Sib 1893 possesses pro- and anticonvulsant activity in the electroshock seizure threshold test in mice. Pol J Pharmacol. 2002 Sep-Oct;54(5):517-20. PubMed PMID: 12593540. 6: O'Leary DM, Movsesyan V, Vicini S, Faden AI. Selective mGluR5 antagonists MPEP and SIB-1893 decrease NMDA or glutamate-mediated neuronal toxicity through actions that reflect NMDA receptor antagonism. Br J Pharmacol. 2000 Dec;131(7):1429-37. PubMed PMID: 11090117; PubMed Central PMCID: PMC1572472. 7: Chapman AG, Nanan K, Williams M, Meldrum BS. 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. 2000 Jul 10;39(9):1567-74. PubMed PMID: 10854901. 8: 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. SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5. J Pharmacol Exp Ther. 1999 Jul;290(1):170-81. PubMed PMID: 10381773.