From Wikipedia, the free encyclopedia
Ditolylguanidine
Clinical data
ATC code
  • none
Identifiers
  • 1,2-bis(2-methylphenyl)guanidine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard ( EPA)
ECHA InfoCard 100.002.344 Edit this at Wikidata
Chemical and physical data
FormulaC15H17N3
Molar mass239.322 g·mol−1
3D model ( JSmol)
  • N(=C(/Nc1ccccc1C)N)\c2ccccc2C
  • InChI=1S/C15H17N3/c1-11-7-3-5-9-13(11)17-15(16)18-14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H3,16,17,18) checkY
  • Key:OPNUROKCUBTKLF-UHFFFAOYSA-N checkY
   (verify)

Ditolylguanidine is a sigma receptor agonist. [1] It is somewhat [2] selective for sigma receptors, but non-selective between the two sigma receptor subtypes, binding to both σ1 and σ2 with equal affinity. [3] It has neuroprotective [4] and antidepressant effects, [5] and potentiates the effects of NMDA antagonists. [6]

See also

References

  1. ^ Weber E, Sonders M, Quarum M, McLean S, Pou S, Keana JF (November 1986). "1,3-Di(2-[5-3H]tolyl)guanidine: a selective ligand that labels sigma-type receptors for psychotomimetic opiates and antipsychotic drugs". Proceedings of the National Academy of Sciences of the United States of America. 83 (22): 8784–8788. Bibcode: 1986PNAS...83.8784W. doi: 10.1073/pnas.83.22.8784. PMC  387016. PMID  2877462.
  2. ^ "1,3-Di-o-tolylguanidine | C15H17N3". PubChem. U.S. National Library of Medicine. Archived from the original on 2021-01-08. Retrieved 2017-06-07.
  3. ^ Glennon RA (October 2005). "Pharmacophore identification for sigma-1 (sigma1) receptor binding: application of the "deconstruction-reconstruction-elaboration" approach". Mini Reviews in Medicinal Chemistry. 5 (10): 927–940. doi: 10.2174/138955705774329519. PMID  16250835.
  4. ^ Katnik C, Guerrero WR, Pennypacker KR, Herrera Y, Cuevas J (December 2006). "Sigma-1 receptor activation prevents intracellular calcium dysregulation in cortical neurons during in vitro ischemia". The Journal of Pharmacology and Experimental Therapeutics. 319 (3): 1355–1365. doi: 10.1124/jpet.106.107557. PMID  16988055. S2CID  14582181.
  5. ^ Skuza G, Rogóz Z (2003). "Sigma1 receptor antagonists attenuate antidepressant-like effect induced by co-administration of 1,3 di-o-tolylguanidine (DTG) and memantine in the forced swimming test in rats". Polish Journal of Pharmacology. 55 (6): 1149–1152. PMID  14730114.
  6. ^ Monnet FP, Morin-Surun MP, Leger J, Combettes L (November 2003). "Protein kinase C-dependent potentiation of intracellular calcium influx by sigma1 receptor agonists in rat hippocampal neurons". The Journal of Pharmacology and Experimental Therapeutics. 307 (2): 705–712. doi: 10.1124/jpet.103.053447. PMID  12975497. S2CID  35397107.
From Wikipedia, the free encyclopedia
Ditolylguanidine
Clinical data
ATC code
  • none
Identifiers
  • 1,2-bis(2-methylphenyl)guanidine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard ( EPA)
ECHA InfoCard 100.002.344 Edit this at Wikidata
Chemical and physical data
FormulaC15H17N3
Molar mass239.322 g·mol−1
3D model ( JSmol)
  • N(=C(/Nc1ccccc1C)N)\c2ccccc2C
  • InChI=1S/C15H17N3/c1-11-7-3-5-9-13(11)17-15(16)18-14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H3,16,17,18) checkY
  • Key:OPNUROKCUBTKLF-UHFFFAOYSA-N checkY
   (verify)

Ditolylguanidine is a sigma receptor agonist. [1] It is somewhat [2] selective for sigma receptors, but non-selective between the two sigma receptor subtypes, binding to both σ1 and σ2 with equal affinity. [3] It has neuroprotective [4] and antidepressant effects, [5] and potentiates the effects of NMDA antagonists. [6]

See also

References

  1. ^ Weber E, Sonders M, Quarum M, McLean S, Pou S, Keana JF (November 1986). "1,3-Di(2-[5-3H]tolyl)guanidine: a selective ligand that labels sigma-type receptors for psychotomimetic opiates and antipsychotic drugs". Proceedings of the National Academy of Sciences of the United States of America. 83 (22): 8784–8788. Bibcode: 1986PNAS...83.8784W. doi: 10.1073/pnas.83.22.8784. PMC  387016. PMID  2877462.
  2. ^ "1,3-Di-o-tolylguanidine | C15H17N3". PubChem. U.S. National Library of Medicine. Archived from the original on 2021-01-08. Retrieved 2017-06-07.
  3. ^ Glennon RA (October 2005). "Pharmacophore identification for sigma-1 (sigma1) receptor binding: application of the "deconstruction-reconstruction-elaboration" approach". Mini Reviews in Medicinal Chemistry. 5 (10): 927–940. doi: 10.2174/138955705774329519. PMID  16250835.
  4. ^ Katnik C, Guerrero WR, Pennypacker KR, Herrera Y, Cuevas J (December 2006). "Sigma-1 receptor activation prevents intracellular calcium dysregulation in cortical neurons during in vitro ischemia". The Journal of Pharmacology and Experimental Therapeutics. 319 (3): 1355–1365. doi: 10.1124/jpet.106.107557. PMID  16988055. S2CID  14582181.
  5. ^ Skuza G, Rogóz Z (2003). "Sigma1 receptor antagonists attenuate antidepressant-like effect induced by co-administration of 1,3 di-o-tolylguanidine (DTG) and memantine in the forced swimming test in rats". Polish Journal of Pharmacology. 55 (6): 1149–1152. PMID  14730114.
  6. ^ Monnet FP, Morin-Surun MP, Leger J, Combettes L (November 2003). "Protein kinase C-dependent potentiation of intracellular calcium influx by sigma1 receptor agonists in rat hippocampal neurons". The Journal of Pharmacology and Experimental Therapeutics. 307 (2): 705–712. doi: 10.1124/jpet.103.053447. PMID  12975497. S2CID  35397107.

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