Ditolylguanidine: Difference between revisions

{{drugbox | verifiedrevid = 399911334

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| image = Ditolylguanidine.png

| InChI = 1/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)

| InChIKey = OPNUROKCUBTKLF-UHFFFAOYAM

| CAS_number = 97-39-2

| ATC_prefix = none

| ATC_suffix =

| PubChem = 7333

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

| molecular_weight = 239.316 g/mol

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

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'''Ditolylguanidine''' is a [[sigma receptor]] agonist.<ref name="pmid2877462">{{cite journal | author = 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 = Proc. Natl. Acad. Sci. U.S.A. | volume = 83 | issue = 22 | pages = 8784–8 | year = 1986 | month = November | pmid = 2877462 | pmc = 387016 | doi = 10.1073/pnas.83.22.8784| url = }}</ref> It is selective for sigma receptors, but non-selective between the two sigma receptor subtypes, binding to both σ1 and σ2 with equal affinity.<ref>{{cite journal | last1 = Glennon | first1 = 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 = 927–40 | year = 2005 | pmid = 16250835 }}</ref> It has [[neuroprotective]]<ref>{{cite journal | last1 = Katnik | first1 = C | last2 = Guerrero | first2 = WR | last3 = Pennypacker | first3 = KR | last4 = Herrera | first4 = Y | last5 = Cuevas | first5 = 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 = 1355–65 | year = 2006 | pmid = 16988055 | doi = 10.1124/jpet.106.107557 }}</ref> and [[antidepressant]] effects,<ref>{{cite journal | last1 = Skuza | first1 = G | last2 = Rogóz | first2 = 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 = 1149–52 | year = 2003 | pmid = 14730114 }}</ref> and potentiates the effects of [[NMDA antagonist]]s.<ref>{{cite journal | last1 = Monnet | first1 = FP | last2 = Morin-Surun | first2 = MP | last3 = Leger | first3 = J | last4 = Combettes | first4 = 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 = 705–12 | year = 2003 | pmid = 12975497 | doi = 10.1124/jpet.103.053447 }}</ref>

==References==

<references/>

[[Category:Sigma agonists]]

[[Category:Guanidines]]

[[Category:Aromatic amines]]

{{pharm-stub}}

[[de:N,N'-Di-o-tolylguanidin]]