Synonym
AI3-51270, Methylguanidine HCl, Methylguanidine hydrochloride
IUPAC/Chemical Name
Guanidine, methyl-, hydrochloride
InChi Key
VJQCNCOGZPSOQZ-UHFFFAOYSA-N
InChi Code
1S/C2H7N3.ClH/c1-5-2(3)4;/h1H3,(H4,3,4,5);1H
SMILES Code
N(C(N)=N)C.Cl
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
Biological target:
Methylguanidine hydrochloride is a biochemical that can be used in the synthesis of biaryl derivatives which were evaluated as BACE1 inhibitors.
In vitro activity:
GMOM (N-(2-chloro-5-thiomethylphenyl)-N'-(3-methoxyphenyl)-N'-methylguanidine) was at least 70-fold more selective for NMDA receptors compared to all other targets examined. In homologous inhibition and concentration-response assays, the binding of [3H]GMOM was regulated by NMDA receptor agonists, albeit in a less prominent manner compared to [3H]MK-801. [3H]MK-801 (2 nmol L-1) was inhibited in a monophasic manner by GMOM under baseline and combined agonist conditions, with an IC50 value of ~19 nmol L-1.
Reference: Pharmacol Res Perspect. 2019 Feb;7(1):e00458. https://pubmed.ncbi.nlm.nih.gov/30784206/
In vivo activity:
The aim of the present study was to evaluate the possible anti-inflammatory activity of MG (methylguanidine) in a model of septic shock induced by lipopolysaccharide (LPS) in mice. NOx levels, evaluated as nitrite/nitrate serum levels, was significantly reduced in MG-treated rats (78.6%, p < 0.0001; n = 10). Immunohistochemistry revealed, in the lung tissue of LPS-treated group, a positive staining for nitrotyrosine and poly(adenosine diphosphate [ADP] ribose) synthase, both of which were reduced in MG-treated mice.
Reference: Free Radic Res. 2004 Nov;38(11):1143-53. https://pubmed.ncbi.nlm.nih.gov/15621690/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
109.56
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. Metaxas A, van Berckel BNM, Klein PJ, Verbeek J, Nash EC, Kooijman EJM, Renjaän VA, Golla SSV, Boellaard R, Christiaans JAM, Windhorst AD, Leysen JE. Binding characterization of N-(2-chloro-5-thiomethylphenyl)-N'-(3-[3 H]3 methoxy phenyl)-N'-methylguanidine ([3 H]GMOM), a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist. Pharmacol Res Perspect. 2019 Feb;7(1):e00458. doi: 10.1002/prp2.458. PMID: 30784206; PMCID: PMC6381215.
2. Noda Y, Masumizu T, Mori A. The Anticonvulsant Zonisamide Inhibits Hydroxyl Radical Generated from Methylguanidine. Acta Med Okayama. 2016 Oct;70(5):371-375. doi: 10.18926/AMO/54595. PMID: 27777429.
3. Marzocco S, Di Paola R, Ribecco MT, Sorrentino R, Domenico B, Genesio M, Pinto A, Autore G, Cuzzocrea S. Effect of methylguanidine in a model of septic shock induced by LPS. Free Radic Res. 2004 Nov;38(11):1143-53. doi: 10.1080/10715760410001725517. PMID: 15621690.
4. Waterhouse RN, Slifstein M, Dumont F, Zhao J, Chang RC, Sudo Y, Sultana A, Balter A, Laruelle M. In vivo evaluation of [11C]N-(2-chloro-5-thiomethylphenyl)-N'-(3-methoxy-phenyl)-N'-methylguanidine ([11C]GMOM) as a potential PET radiotracer for the PCP/NMDA receptor. Nucl Med Biol. 2004 Oct;31(7):939-48. doi: 10.1016/j.nucmedbio.2004.03.012. PMID: 15464396.
In vitro protocol:
1. Metaxas A, van Berckel BNM, Klein PJ, Verbeek J, Nash EC, Kooijman EJM, Renjaän VA, Golla SSV, Boellaard R, Christiaans JAM, Windhorst AD, Leysen JE. Binding characterization of N-(2-chloro-5-thiomethylphenyl)-N'-(3-[3 H]3 methoxy phenyl)-N'-methylguanidine ([3 H]GMOM), a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist. Pharmacol Res Perspect. 2019 Feb;7(1):e00458. doi: 10.1002/prp2.458. PMID: 30784206; PMCID: PMC6381215.
2. Noda Y, Masumizu T, Mori A. The Anticonvulsant Zonisamide Inhibits Hydroxyl Radical Generated from Methylguanidine. Acta Med Okayama. 2016 Oct;70(5):371-375. doi: 10.18926/AMO/54595. PMID: 27777429.
In vivo protocol:
1. Marzocco S, Di Paola R, Ribecco MT, Sorrentino R, Domenico B, Genesio M, Pinto A, Autore G, Cuzzocrea S. Effect of methylguanidine in a model of septic shock induced by LPS. Free Radic Res. 2004 Nov;38(11):1143-53. doi: 10.1080/10715760410001725517. PMID: 15621690.
2. Waterhouse RN, Slifstein M, Dumont F, Zhao J, Chang RC, Sudo Y, Sultana A, Balter A, Laruelle M. In vivo evaluation of [11C]N-(2-chloro-5-thiomethylphenyl)-N'-(3-methoxy-phenyl)-N'-methylguanidine ([11C]GMOM) as a potential PET radiotracer for the PCP/NMDA receptor. Nucl Med Biol. 2004 Oct;31(7):939-48. doi: 10.1016/j.nucmedbio.2004.03.012. PMID: 15464396.
1: Bosco AM, Almeida BFM, Pereira PP, Dos Santos DB, Neto ÁJS, Ferreira WL, Ciarlini PC. The uremic toxin methylguanidine increases the oxidative metabolism and accelerates the apoptosis of canine neutrophils. Vet Immunol Immunopathol. 2017 Mar;185:14-19. doi: 10.1016/j.vetimm.2017.01.006. Epub 2017 Jan 28. PubMed PMID: 28241998.
2: Noda Y, Masumizu T, Mori A. The Anticonvulsant Zonisamide Inhibits Hydroxyl Radical Generated from Methylguanidine. Acta Med Okayama. 2016 Oct;70(5):371-375. PubMed PMID: 27777429.
3: Oshima N, Onimaru H, Matsubara H, Uchida T, Watanabe A, Takechi H, Nishida Y, Kumagai H. Uric acid, indoxyl sulfate, and methylguanidine activate bulbospinal neurons in the RVLM via their specific transporters and by producing oxidative stress. Neuroscience. 2015 Sep 24;304:133-45. doi: 10.1016/j.neuroscience.2015.07.055. Epub 2015 Jul 28. PubMed PMID: 26208844.
4: Marzocco S, Di Paola R, Serraino I, Sorrentino R, Meli R, Mattaceraso G, Cuzzocrea S, Pinto A, Autore G. Effect of methylguanidine in carrageenan-induced acute inflammation in the rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):341-50. PubMed PMID: 14744621.
