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 ;
UNII	LL2P01I17O;
ChEMBL	ChEMBL282433 ;
CompTox Dashboard (EPA)	DTXSID2026606 ;
ECHA InfoCard	100.002.344
Chemical and physical data
Formula	C15H17N3
Molar mass	239.322 g·mol−1
3D model (JSmol)	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 ;
	(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]

References

^ 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.
^ "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.
^ 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.
^ 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.
^ 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.
^ 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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[pmid2877462-1] 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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v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators

See also

References