52378-40-2

Basic information

• Product Name: N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea
• Synonyms: N-Cyano-S-methyl-N''-[2-(4-methyl-5-imidazolyl)-methylthioethyl]- isothioure;2-Methyl-1-cyano-3-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]isothiourea;N1-[2-[(5-Methyl-1H-imidazole-4-yl)methylthio]ethyl]-N2-cyano(methylthio)methanamidine;Einecs 257-889-5;N-Cyano-N-[2-(5-MethyliMidazole-4-Methylthio)ethyl]-S-Methyl isothiourea Monohydrate;N-Cyano-N'-[2-[(4-methyl-5-imidazolyl)methylthio]ethyl]-S-methylisothiourea;N-Cyano-N'-[2-[[(5-methyl-4-imidazolyl)methyl]thio]ethyl]-S-methylisothiourea;S-Methyl-N-cyano-N'-[2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethyl]isothiourea
• CAS NO: 52378-40-2
• Molecular Formula: C₁₀H₁₅N₅S₂
• Molecular Weight: 269.3896
• EINECS: 257-889-5
• Mol File: 52378-40-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 148-150℃
• Boiling Point: 501.5 °C at 760 mmHg
• Flash Point: 257.1 °C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.44E-10mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.11±0.10(Predicted)
• CAS DataBase Reference: N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea(52378-40-2)
• EPA Substance Registry System: N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea(52378-40-2)

Safety Data

• Hazardous Substances Data: 52378-40-2(Hazardous Substances Data)

Usage

Description

N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea, also known as Cimetidine EP Impurity A, is a chemical compound related to Cimetidine (C441650). It is derived from the synthesis process of Cimetidine, a well-known histamine H2-receptor antagonist. This impurity is characterized by its unique chemical structure, which includes a cyano group, an isothiourea moiety, and a methylthio-substituted imidazole ring.

Uses

Used in Pharmaceutical Industry:
N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea is used as a reference compound for the identification and quantification of impurities in the manufacturing process of Cimetidine (C441650). As a related impurity, it helps ensure the quality, safety, and efficacy of the final drug product by providing a benchmark for purity and consistency.
Used in Research and Development:
In the field of pharmaceutical research and development, N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea serves as a valuable tool for studying the structure-activity relationship of histamine H2-receptor antagonists. This understanding can lead to the design and development of new, more effective medications with improved pharmacological properties.
Used in Quality Control:
N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea is used as a reference material in the quality control of Cimetidine (C441650) and its formulations. It aids in the development and validation of analytical methods, such as high-performance liquid chromatography (HPLC) and mass spectrometry, to accurately measure and control the levels of impurities in the final drug product.
Used in the Preparation of Histamine H2 Receptor Antagonists:
Although N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea is an impurity, it may also be used in the synthesis and preparation of novel histamine H2 receptor antagonists. By studying its chemical properties and interactions, researchers can gain insights into the design of new compounds with potential therapeutic applications in the treatment of conditions such as peptic ulcers, gastroesophageal reflux disease (GERD), and other acid-related disorders.

InChI:InChI=1/C10H15N5S2/c1-8-9(15-7-14-8)5-17-4-3-12-10(16-2)13-6-11/h7H,3-5H2,1-2H3,(H,12,13)(H,14,15)

Upstream product

• 38603-72-4 2-[((5-methyl-1H-imidazol-4-yl)methyl)thio]ethanamine dihydrochloride 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 
• 38585-67-0 4-{[(2-aminoethyl)thio]methyl}-5-methylimidazole 
• 38585-67-0 4-methyl-5-<(2-aminoethyl)-thiomethyl>-imidazole 

Downstream Products

• 52378-43-5 N-Cyano-N'-<2-<(5(4)-methyl-4(5)-imidazolyl)-methylthio>-ethyl>-guanidin 
• 51481-61-9 Cimetidine 
• 52378-43-5 N-Cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-guanidine 
• 270574-63-5 cimetidine 
• 51481-61-9 Cimetidine 

Relevant articles and documents

Importance of the azole moiety of cimetidine derivatives for the inhibition of human multidrug and toxin extrusion transporter 1 (hmate1)

Herein, we describe the design and synthesis of cimetidine analogs, as well as their inhibitory activity toward the human multidrug and toxin extrusion transporter 1 (hMATE1), which is related to nephrotoxicity of drugs. Cimetidine is the histamine H2-receptor antagonist, but also inhibits hMATE1, which is known to cause renal impairment. We designed and synthesized cimetidine analogs to evaluate hMATE1 inhibitory activity to reveal whether the analogs could reduce the inhibition of hMATE1. The results showed that all analogs with an unsubstituted guanidino group exhibited hMATE1 inhibitory activity. On the other hand, there was a clear difference in the hMATE1 inhibitory activity for the other compounds. That is, compounds with a methylimidazole ring exhibited hMATE1 inhibition, while compounds with a phenyl ring did not. The results suggest that the ability to form hydrogen bonds at the azole moiety is strongly involved in the hMATE1 inhibition.

H2-Antihistaminics, XXXV: Synthesis and H2-antagonistic activity of imidazolylmethylthioalkyl-substituted 1,2,4-triazoles

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Process for preparing 5-methyl-4-imidazolecarboxylic acid esters

A process for the preparation of 5-methyl-4-imidazolecarboxylic acid esters from acetoacetic acid esters. The products of this process are useful as intermediates for preparing cimetidine.