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

Uses

N-Cyano-N’-[2-[(4-methyl-5-imidazolyl)methylthio]ethyl]-S-methylisothiourea (Cimetidine EP Impurity A) is a Cimetidine (C441650) related impurity. Cimetidine (C441650), a competitive histamine H2-receptor antagonist which inhibits gastric acid secretion and reduces pepsin output. Also used in the preparation of histamine H2 receptor antagonists.

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

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

Downstream Products

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

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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Synthesis and h2-antihistaminic activity of n,n'-bisimidazole-substituted thioureas, cyanoguanidines and 2-nitro-1,1-ethenediamines 10. C: H2-antihistaminics

In studies on structure-activity relationships of histamine H2-receptor antagonists, N,N'-bis(2-[(4-imidazolyl)-methylthio]-ethyl)-substituted thioureas, cyanoguinidines, and 2-nitro-1,1-ethenediamines with different C-5 methylation of the imidazole rings were prepared and tested for their H2-antihistaminic activity on the isolated guinea-pig atrium and the stimulated gastric acid secretion of the anaesthetized rat. When tested on isolated guinea-pig atrium, substances with both C-5 positions methylated (5b, 7b, 9b) proved to be up to seven times more active than metiamide, whereas inhibition of gastric acid secretion turned out to be less marked. While equally methylated thioureas and cyanoguanidines showed same potency, the 2-nitro-1,1-ethenediamines clearly possessed lower activity.