ditolylguanidine

{{Short description|Experimental drug}}

{{Drugbox

| verifiedrevid = 414433472

| IUPAC_name = 1,2-bis(2-methylphenyl)guanidine

| image = 1,3-Ditolylguanidine.svg

| width = 200

| image2 = Ditolylguanidine 3D BS.png

| width2 = 200

| tradename =

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| legal_UK =

| legal_US =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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| IUPHAR_ligand = 6684

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 97-39-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = LL2P01I17O

| ATC_prefix = none

| ATC_suffix =

| PubChem = 7333

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 7056

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 282433

| C=15 | H=17 | N=3

| smiles = N(=C(/Nc1ccccc1C)N)\c2ccccc2C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OPNUROKCUBTKLF-UHFFFAOYSA-N

| melting_point =

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}}

Ditolylguanidine is a sigma receptor agonist.{{cite journal | vauthors = Weber E, Sonders M, Quarum M, McLean S, Pou S, Keana JF | title = 1,3-Di(2-[5-3H]tolyl)guanidine: a selective ligand that labels sigma-type receptors for psychotomimetic opiates and antipsychotic drugs | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 83 | issue = 22 | pages = 8784–8788 | date = November 1986 | pmid = 2877462 | pmc = 387016 | doi = 10.1073/pnas.83.22.8784 | bibcode = 1986PNAS...83.8784W | doi-access = free }} It is somewhat{{Cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/7333#section=BioAssay-Results |title=1,3-Di-o-tolylguanidine {{!}} C15H17N3 | work = PubChem | publisher = U.S. National Library of Medicine |language=en|access-date=2017-06-07|archive-date=2021-01-08|archive-url=https://web.archive.org/web/20210108060333/https://pubchem.ncbi.nlm.nih.gov/compound/7333#section=BioAssay-Results|url-status=live}} selective for sigma receptors, but non-selective between the two sigma receptor subtypes, binding to both σ1 and σ2 with equal affinity.{{cite journal | vauthors = Glennon RA | title = Pharmacophore identification for sigma-1 (sigma1) receptor binding: application of the "deconstruction-reconstruction-elaboration" approach | journal = Mini Reviews in Medicinal Chemistry | volume = 5 | issue = 10 | pages = 927–940 | date = October 2005 | pmid = 16250835 | doi = 10.2174/138955705774329519 }} It has neuroprotective{{cite journal | vauthors = Katnik C, Guerrero WR, Pennypacker KR, Herrera Y, Cuevas J | title = Sigma-1 receptor activation prevents intracellular calcium dysregulation in cortical neurons during in vitro ischemia | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 319 | issue = 3 | pages = 1355–1365 | date = December 2006 | pmid = 16988055 | doi = 10.1124/jpet.106.107557 | s2cid = 14582181 }} and antidepressant effects,{{cite journal | vauthors = Skuza G, Rogóz Z | title = 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 | journal = Polish Journal of Pharmacology | volume = 55 | issue = 6 | pages = 1149–1152 | year = 2003 | pmid = 14730114 }} and potentiates the effects of NMDA antagonists.{{cite journal | vauthors = Monnet FP, Morin-Surun MP, Leger J, Combettes L | title = Protein kinase C-dependent potentiation of intracellular calcium influx by sigma1 receptor agonists in rat hippocampal neurons | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 2 | pages = 705–712 | date = November 2003 | pmid = 12975497 | doi = 10.1124/jpet.103.053447 | s2cid = 35397107 }}