54252-45-8

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-dimethyl-2-nitro-1,1-ethenediamine is used as an impurity in the production of histamine H2-receptor antagonists for the pharmaceutical industry. Its presence is significant as it can impact the quality, safety, and efficacy of the final drug product. The application reason for its use in this context is to ensure that the manufacturing process of Nizatidine and Ranitidine is monitored and controlled to minimize the presence of this impurity, thereby maintaining the therapeutic benefits and reducing potential side effects of the medications.

Upstream product

• 74-89-5 methylamine 
• 13623-94-4 1,1-di(methylsulfanyl)-2-nitroethylene 
• 102721-76-6 2-methylamino-2-methylthio-1-nitroethene 

Downstream Products

• 54252-35-6 [3-(4-chloro-phenyl)-4-nitro-isoxazol-5-yl]-methyl-amine 
• 64030-91-7 3,3-bis-methylamino-2-nitro-N-phenyl-thioacrylamide 
• 73923-23-6 C₁₀H₁₃N₅O₂ 
• 141642-90-2 (E)-N-(3,3-Bis-methylamino-2-nitro-thioacryloyl)-3-(4-methoxy-phenyl)-acrylamide 
• 141642-88-8 (E)-N-(3,3-Bis-methylamino-2-nitro-thioacryloyl)-3-phenyl-acrylamide 

Relevant academic research and scientific papers

THE DIPOLE MOMENTS OF 1,3-DIMETHYLTHIOUREA, 1,3-DIMETHYL-2-CYANOGUANIDINE AND 1,1-BIS-METHYLAMINO-2-NITROETHENE IN AQUEOUS SOLUTION

The dipole moments, ν, of 1,3-dimethylthiourea, 1,3-dimethyl-2-cyanoguanidine and 1,1-bis-methylamino-2-nitroethene which are important partial structures of histamine H2 receptor antagonist drugs have been determined in aqueous solution at 25 deg C from static permittivities measured over a wide frequency range.The dipole moments were respectively 10.0, 13.1 and 15.1 Debyes, suggesting that each compound has a high degree of zwitterionic character in water.

MECHANISM OF H/D EXCHANGE AND VINYLIC SUBSTITUTION IN 2,2-DISUBSTITUTED NITROETHYLENE AND RELATED STUDIES

Rate measurements for H/D exchange at the α-C atom of the nitroethylenic moiety in ranitidine, 2 (a histaminic H2-receptor antagonist with ulcerostatic activity), and in the model compounds 3a, 3b have revealed pseudo-first order, pH-dependent kinetics.These data have been interpreted in terms of an acid-catalysed intramolecular proton (deuterium) transfer within the nitrolic form of the compounds investigated with inversion of configuration at the carbon-carbon double bond.Qualitative studies of the rates of nucleophilic substitution at the vinylic β-C atom in 2,2-bismethylthio-1-nitroethylene (3a) and 2,2-bismethylthio-N-cyanoazomethine (4a) with methylamine, revealed inversion of the relative rates of the first and second substitution step.The result has been rationalized as due to a change from addition-elimination to β,γ-elimination-addition mechanism.HMO calculations of the ?-electron densities and ?-bond orders in 3a-3c and 4a-4c support this rationalization.