Ditolylguanidine | DTG | CAS#97-39-2 | Sigma receptor ligand

MedKoo Cat#: 463226 | Name: Ditolylguanidine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

1,3-Di-o-tolylguanidine (DTG) is a sigma (σ) receptor ligand. In vivo, DTG increases latency to tail withdrawal in the tail flick test and induces hypothermia in mice. It decreases infarct size and increases the number of cortical and hippocampal NeuN-positive neurons in a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).

Chemical Structure

Ditolylguanidine

CAS#97-39-2

Theoretical Analysis

MedKoo Cat#: 463226

Name: Ditolylguanidine

CAS#: 97-39-2

Chemical Formula: C15H17N3

Exact Mass: 239.1422

Molecular Weight: 239.32

Elemental Analysis: C, 75.28; H, 7.16; N, 17.56

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 450.00	2 Weeks

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Related CAS #

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Synonym

Ditolylguanidine; DTG; 1,3-Di-o-tolylguanidine; Di-o-tolylguanidine; DOTG; NSC 132023; NSC132023; NSC-132023; NSC 473; NSC473; NSC-473;

IUPAC/Chemical Name

1,2-bis(2-methylphenyl)guanidine

InChi Key

OPNUROKCUBTKLF-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

N/C(NC1=CC=CC=C1C)=N\C2=CC=CC=C2C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ditolylguanidine (1,3-Di-o-tolylguanidine) is an agonist of sigma receptor (σ1/σ2 receptor).

In vitro activity:

Here, this study shows that the nonselective σ receptor agonist ditolylguanidine, and the selective σ1 receptor agonist PRE-084, inhibit the osmotic swelling of Müller cell somata induced by superfusion of rat retinal slices with a hypoosmotic solution containing barium ions. Reference: Neurosci Lett. 2016 Jan 1;610:13-8. https://pubmed.ncbi.nlm.nih.gov/26499958/

In vivo activity:

Infarct areas were quantified at the level of the cortical/striatal and cortical/hippocampal regions in control (MCAO-only) and DTG treated animals using a marker for neurodegeneration, Fluoro-Jade. DTG treatment significantly reduced infarct area in both cortical/striatal and cortical/hippocampal regions by >80%, relative to control rats. Reference: Curr Neurovasc Res. 2006 May;3(2):89-98. https://pubmed.ncbi.nlm.nih.gov/16719792/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	125.35
	DMSO	90.0	376.06
	Ethanol	1.0	4.18

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 239.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Vogler S, Winters H, Pannicke T, Wiedemann P, Reichenbach A, Bringmann A. Sigma-1 receptor activation inhibits osmotic swelling of rat retinal glial (Müller) cells by transactivation of glutamatergic and purinergic receptors. Neurosci Lett. 2016 Jan 1;610:13-8. doi: 10.1016/j.neulet.2015.10.042. Epub 2015 Nov 4. PMID: 26499958. 3. Ajmo CT Jr, Vernon DO, Collier L, Pennypacker KR, Cuevas J. Sigma receptor activation reduces infarct size at 24 hours after permanent middle cerebral artery occlusion in rats. Curr Neurovasc Res. 2006 May;3(2):89-98. doi: 10.2174/156720206776875849. PMID: 16719792. 4. Kest B, Mogil JS, Sternberg WF, Pechnick RN, Liebeskind JC. Antinociception following 1,3,-di-o-tolylguanidine, a selective sigma receptor ligand. Pharmacol Biochem Behav. 1995 Apr;50(4):587-92. doi: 10.1016/0091-3057(94)00346-7. PMID: 7617705.

In vitro protocol:

In vivo protocol:

1. Ajmo CT Jr, Vernon DO, Collier L, Pennypacker KR, Cuevas J. Sigma receptor activation reduces infarct size at 24 hours after permanent middle cerebral artery occlusion in rats. Curr Neurovasc Res. 2006 May;3(2):89-98. doi: 10.2174/156720206776875849. PMID: 16719792. 2. Kest B, Mogil JS, Sternberg WF, Pechnick RN, Liebeskind JC. Antinociception following 1,3,-di-o-tolylguanidine, a selective sigma receptor ligand. Pharmacol Biochem Behav. 1995 Apr;50(4):587-92. doi: 10.1016/0091-3057(94)00346-7. PMID: 7617705.

1: Valenza M, Blasio A, DiLeo A, Cottone P, Sabino V. Sigma receptor-induced heavy drinking in rats: Modulation by the opioid receptor system. Pharmacol Biochem Behav. 2020 May;192:172914. doi: 10.1016/j.pbb.2020.172914. Epub 2020 Mar 20. PMID: 32205151. 2: Sieira BJ, Montes R, Touffet A, Rodil R, Cela R, Gallard H, Quintana JB. Chlorination and bromination of 1,3-diphenylguanidine and 1,3-di-o- tolylguanidine: Kinetics, transformation products and toxicity assessment. J Hazard Mater. 2020 Mar 5;385:121590. doi: 10.1016/j.jhazmat.2019.121590. Epub 2019 Nov 13. PMID: 31784125. 3: Schulze S, Zahn D, Montes R, Rodil R, Quintana JB, Knepper TP, Reemtsma T, Berger U. Occurrence of emerging persistent and mobile organic contaminants in European water samples. Water Res. 2019 Apr 15;153:80-90. doi: 10.1016/j.watres.2019.01.008. Epub 2019 Jan 18. PMID: 30703676. 4: Zeng C, Weng CC, Schneider ME Jr, Puentes L, Riad A, Xu K, Makvandi M, Jin L, Hawkins WG, Mach RH. TMEM97 and PGRMC1 do not mediate sigma-2 ligand-induced cell death. Cell Death Discov. 2019 Jan 28;5:58. doi: 10.1038/s41420-019-0141-2. PMID: 30701090; PMCID: PMC6349905. 5: Kokornaczyk AK, Schepmann D, Yamaguchi J, Itami K, Laurini E, Fermeglia M, Pricl S, Wünsch B. Thiazole-Based σ1 Receptor Ligands: Diversity by Late-Stage C-H Arylation of Thiazoles, Structure-Affinity and Selectivity Relationships, and Molecular Interactions. ChemMedChem. 2017 Jul 6;12(13):1070-1080. doi: 10.1002/cmdc.201700166. Epub 2017 Jun 22. PMID: 28544475. 6: Hong WC, Yano H, Hiranita T, Chin FT, McCurdy CR, Su TP, Amara SG, Katz JL. The sigma-1 receptor modulates dopamine transporter conformation and cocaine binding and may thereby potentiate cocaine self-administration in rats. J Biol Chem. 2017 Jul 7;292(27):11250-11261. doi: 10.1074/jbc.M116.774075. Epub 2017 May 11. PMID: 28495886; PMCID: PMC5500793. 7: Katz JL, Hiranita T, Kopajtic TA, Rice KC, Mesangeau C, Narayanan S, Abdelazeem AH, McCurdy CR. Blockade of Cocaine or σ Receptor Agonist Self Administration by Subtype-Selective σ Receptor Antagonists. J Pharmacol Exp Ther. 2016 Jul;358(1):109-24. doi: 10.1124/jpet.116.232728. Epub 2016 Apr 21. PMID: 27189970; PMCID: PMC4931880. 8: Chu UB, Mavlyutov TA, Chu ML, Yang H, Schulman A, Mesangeau C, McCurdy CR, Guo LW, Ruoho AE. The Sigma-2 Receptor and Progesterone Receptor Membrane Component 1 are Different Binding Sites Derived From Independent Genes. EBioMedicine. 2015 Oct 19;2(11):1806-13. doi: 10.1016/j.ebiom.2015.10.017. PMID: 26870805; PMCID: PMC4740303. 9: Jaramillo-Loranca BE, Garcés-Ramírez L, Munguía Rosales AA, Luna Ramírez C, Vargas Hernández G, Morales-Dionisio O, González-Elizalde K, Flores G, Zamudio S, De La Cruz-López F. The sigma agonist 1,3-di-o-tolyl-guanidine reduces the morphological and behavioral changes induced by neonatal ventral hippocampus lesion in rats. Synapse. 2015 Apr;69(4):213-25. doi: 10.1002/syn.21811. Epub 2015 Feb 28. PMID: 25682743. 10: Moritz C, Berardi F, Abate C, Peri F. Live imaging reveals a new role for the sigma-1 (σ1) receptor in allowing microglia to leave brain injuries. Neurosci Lett. 2015 Mar 30;591:13-18. doi: 10.1016/j.neulet.2015.02.004. Epub 2015 Feb 7. PMID: 25666889. 11: Behensky AA, Yasny IE, Shuster AM, Seredenin SB, Petrov AV, Cuevas J. Afobazole activation of σ-1 receptors modulates neuronal responses to amyloid-β25-35. J Pharmacol Exp Ther. 2013 Nov;347(2):468-77. doi: 10.1124/jpet.113.208330. Epub 2013 Sep 4. PMID: 24006338. 12: Banister SD, Manoli M, Barron ML, Werry EL, Kassiou M. N-substituted 8-aminopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecanes as σ receptor ligands with potential neuroprotective effects. Bioorg Med Chem. 2013 Oct 1;21(19):6038-52. doi: 10.1016/j.bmc.2013.07.045. Epub 2013 Aug 6. PMID: 23981939. 13: Daviaud N, Garbayo E, Schiller PC, Perez-Pinzon M, Montero-Menei CN. Organotypic cultures as tools for optimizing central nervous system cell therapies. Exp Neurol. 2013 Oct;248:429-40. doi: 10.1016/j.expneurol.2013.07.012. Epub 2013 Jul 27. PMID: 23899655. 14: Gao XF, Yao JJ, He YL, Hu C, Mei YA. Sigma-1 receptor agonists directly inhibit Nav1.2/1.4 channels. PLoS One. 2012;7(11):e49384. doi: 10.1371/journal.pone.0049384. Epub 2012 Nov 5. PMID: 23139844; PMCID: PMC3489664. 15: Ruscher K, Inácio AR, Valind K, Rowshan Ravan A, Kuric E, Wieloch T. Effects of the sigma-1 receptor agonist 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)-piperazine dihydro-chloride on inflammation after stroke. PLoS One. 2012;7(9):e45118. doi: 10.1371/journal.pone.0045118. Epub 2012 Sep 18. PMID: 23028794; PMCID: PMC3445585. 16: Kaushal N, Seminerio MJ, Robson MJ, McCurdy CR, Matsumoto RR. Pharmacological evaluation of SN79, a sigma (σ) receptor ligand, against methamphetamine-induced neurotoxicity in vivo. Eur Neuropsychopharmacol. 2013 Aug;23(8):960-71. doi: 10.1016/j.euroneuro.2012.08.005. Epub 2012 Aug 24. PMID: 22921523; PMCID: PMC3748261. 17: Tsao HH, Skovronsky DM, Lin KJ, Yen TC, Wey SP, Kung MP. Sigma receptor binding of tetrabenazine series tracers targeting VMAT2 in rat pancreas. Nucl Med Biol. 2011 Oct;38(7):1029-34. doi: 10.1016/j.nucmedbio.2011.03.006. Epub 2011 Jun 22. PMID: 21982574. 18: Hiranita T, Soto PL, Tanda G, Katz JL. Lack of cocaine-like discriminative- stimulus effects of σ-receptor agonists in rats. Behav Pharmacol. 2011 Sep;22(5-6):525-30. doi: 10.1097/FBP.0b013e328349ab22. PMID: 21808192; PMCID: PMC3666342. 19: Cuevas J, Behensky A, Deng W, Katnik C. Afobazole modulates neuronal response to ischemia and acidosis via activation of sigma-1 receptors. J Pharmacol Exp Ther. 2011 Oct;339(1):152-60. doi: 10.1124/jpet.111.182774. Epub 2011 Jun 29. PMID: 21715562. 20: Johannessen M, Fontanilla D, Mavlyutov T, Ruoho AE, Jackson MB. Antagonist action of progesterone at σ-receptors in the modulation of voltage-gated sodium channels. Am J Physiol Cell Physiol. 2011 Feb;300(2):C328-37. doi: 10.1152/ajpcell.00383.2010. Epub 2010 Nov 17. Erratum in: Am J Physiol Cell Physiol. 2013 Nov 1;305(9):C997. PMID: 21084640; PMCID: PMC3043630.