Ditolylguanidine

Ditolylguanidine

Clinical data
ATC code	none
Identifiers
IUPAC name 1,2-bis(2-methylphenyl)guanidine
CAS Number	97-39-2
PubChem (CID)	7333
IUPHAR/BPS	6684
ChemSpider	7056
ChEMBL	CHEMBL282433
ECHA InfoCard	100.002.344
Chemical and physical data
Formula	C15H17N3
Molar mass	239.316 g/mol
3D model (Jmol)	Interactive image
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) Key:OPNUROKCUBTKLF-UHFFFAOYSA-N
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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.