Ditolylguanidine

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 InfoCard100.002.344 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]

  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.