553-83-3

Basic information

• Product Name: N-[Amino(imino)methyl]pyrrolidine-1-carboximidamide
• Synonyms: N-[Amino(imino)methyl]pyrrolidine-1-carboximidamide;N-(diaminomethylene)-1-pyrrolidinecarboxamidine;N-(diaminomethylene)pyrrolidine-1-carboxamidine;N-(diaminomethylidene)pyrrolidine-1-carboximidamide;N-CARBAMIMIDOYLPYRROLIDINE-1-CARBOXIMIDAMIDE;N-(Imino-pyrrolidin-1-yl-methyl)-guanidine
• CAS NO: 553-83-3
• Molecular Formula: C₆H₁₃N₅
• Molecular Weight: 155.20092
• Mol File: 553-83-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-[Amino(imino)methyl]pyrrolidine-1-carboximidamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[Amino(imino)methyl]pyrrolidine-1-carboximidamide(553-83-3)
• EPA Substance Registry System: N-[Amino(imino)methyl]pyrrolidine-1-carboximidamide(553-83-3)

Safety Data

• Hazardous Substances Data: 553-83-3(Hazardous Substances Data)

Upstream product

• 25150-61-2 pyrrolidine hydrochloride 
• 127099-85-8 N-Cyanoguanidine 
• 123-75-1 pyrrolidine 

Downstream Products

• 140161-21-3 4-phenyl-6-(pyrrolidin-1-yl)-1,3,5-triazin-2-amine 
• 871332-17-1 4-({[2-amino-4-(pyrrolidin-1-yl)-1,3,5-triazin-6-yl]methyl}amino)benzoic acid 
• 871332-20-6 4-({[2-amino-4-(pyrrolidin-1-yl)-1,3,5-triazin-6-yl]methyl}methylamino)benzoic acid 

Relevant articles and documents

Synthesis and in Vitro AMPK Activation of Cycloalkyl/Alkarylbiguanides with Robust in Vivo Antihyperglycemic Action

This work describes the design, synthesis in one step, and the in vitro, in vivo, and in silico antidiabetic evaluation of a series of ten alicyclic and aromatic (alkyl +aryl: alkaryl)biguanides, analogues of metformin and phenformin. The design was conceived using isosteric replacement, chain-ring transformation, and lower and higher homologation strategies. All compounds were obtained as crystals and their structure was confirmed on the basis of their spectral data (NMR and mass spectra), and their purity was ascertained by microanalysis. Compounds were in vitro evaluated as activators of AMP-Activated Protein Kinase (AMPK). The results indicated that compounds 4, 5, and 6 showed similar or even better effect compared to metformin. Docking analysis was performed with regulatory subunit γ of AMPK, showing several interactions with nucleotide binding pocket. The in vivo evaluation of compounds 4-6 at a single dose of 50 mg/kg was performed in a murine experimental model of diabetes. The results showed an important and robust decrease of plasmatic glucose levels (-40%). Compound 6 was selected for an oral glucose tolerance test, showing an antihyperglycemic effect similar to metformin. The in vivo results indicated that compounds 4-6 may be effective in treating experimental T2DM.

Biguanides and derivatives thereof as inhibitors of advanced glycosylation of a target protein

The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.