Ditolylguanidine

Ditolylguanidine

Systematic (IUPAC) name
1,2-bis(2-methylphenyl)guanidine
Clinical data
Legal status	?
Identifiers
CAS number	97-39-2 Y
ATC code	None
PubChem	CID 7333
ChemSpider	7056 Y
ChEMBL	CHEMBL282433 Y
Chemical data
Formula	C15H17N3
Mol. mass	239.316 g/mol
SMILES N(=C(/Nc1ccccc1C)N)\c2ccccc2C
InChI 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) Y Key:OPNUROKCUBTKLF-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

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

See also

• Aptiganel

References

1. ↑ Weber E, Sonders M, Quarum M, McLean S, Pou S, Keana JF (November 1986). "1,3-Di(2-5-3Htolyl)guanidine: a selective ligand that labels sigma-type receptors for psychotomimetic opiates and antipsychotic drugs". Proc. Natl. Acad. Sci. U.S.A. 83 (22): 8784–8. doi:10.1073/pnas.83.22.8784. PMC 387016. PMID 2877462. 
2. ↑ Glennon, RA (2005). "Pharmacophore identification for sigma-1 (sigma1) receptor binding: application of the "deconstruction-reconstruction-elaboration" approach". Mini reviews in medicinal chemistry 5 (10): 927–40. doi:10.2174/138955705774329519. PMID 16250835. 
3. ↑ Katnik, C; Guerrero, WR; Pennypacker, KR; Herrera, Y; Cuevas, J (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): 1355–65. doi:10.1124/jpet.106.107557. PMID 16988055. 
4. ↑ 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): 1149–52. PMID 14730114. 
5. ↑ Monnet, FP; Morin-Surun, MP; Leger, J; Combettes, L (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): 705–12. doi:10.1124/jpet.103.053447. PMID 12975497.