38603-72-4

Basic information

• Product Name: 2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethylamine dihydrochloride
• Synonyms: 2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethylamine dihydrochloride;2-[[(5-Methyl-1H-imidazol-4-yl)methyl]thio]-ethanamine Dihydrochloride;4-[(2-Aminoethyl)thiomethyl]-5-methylimidazole Dihydrochloride;5-[[(2-Aminoethyl)thio]methyl]-4-methylimidazole Dihydrochloride;Cimetidine impurity J;(2-([(4-METHYL-1H-IMIDAZOL-5-YL)METHYL]THIO)ETHYL)AMINE 2HCL;Cimetidine Impurity J(EP)
• CAS NO: 38603-72-4
• Molecular Formula: C₇H₁₃N₃S*2ClH
• Molecular Weight: 244.1851
• EINECS: 254-033-2
• Product Categories: Chemical Amines;Amines;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 38603-72-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 190-193 °C
• Boiling Point: 400.3°Cat760mmHg
• Flash Point: 195.9°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1.29E-06mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethylamine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethylamine dihydrochloride(38603-72-4)
• EPA Substance Registry System: 2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethylamine dihydrochloride(38603-72-4)

Safety Data

• Hazardous Substances Data: 38603-72-4(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

4-Methyl-5-[(2-aminoethyl)thiomethyl]imidazole Dihydrochloride (cas# 38603-72-4) is a compound useful in organic synthesis.

InChI:InChI=1/C7H13N3S.2ClH/c1-6-7(10-5-9-6)4-11-3-2-8;;/h5H,2-4,8H2,1H3,(H,9,10);2*1H

Upstream product

• 66780-85-6 4-(N,N-dimethylaminomethyl)-5-methylimidazole 
• 60-23-1 Cysteamine 
• 66780-83-4 C-(5-methyl-1⁽³⁾H-imidazol-4-yl)-methylamine 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 38585-62-5 4-hydroxymethyl-5-methylimidazole hydrochloride 
• 51605-33-5 4-methyl-5-chloromethyl-imidazole hydrochloride 
• 822-36-6 4-methyl-1H-imidazole 
• 23187-14-6 4-methylimidazole hydrochloride 

Downstream Products

• 34839-70-8 metiamide 
• 51481-61-9 Cimetidine 
• 270574-63-5 cimetidine 
• 270574-63-5 cimetidine 
• 130106-88-6 4-Bromo-2-{[(E)-2-(5-methyl-1H-imidazol-4-ylmethylsulfanyl)-ethylimino]-methyl}-phenol 
• 52378-40-2 N-cyano-S-methyl-N'-<2-<<(5-methyl-1H-imidazol-4-yl)methyl>thio>ethyl>isothiourea 
• 52378-40-2 N-Cyano-N'-<2-<(5(4)-methyl-4(5)-imidazolyl)-methylthio>-ethyl>-S-methyl-isothioharnstoff 
• 130106-85-3 2-{[(E)-2-(5-Methyl-1H-imidazol-4-ylmethylsulfanyl)-ethylimino]-methyl}-phenol 
• 110821-25-5 N-<2<<(5-methyl-1H-imidazol-4-yl)methyl>thio>ethyl>-N'-cyano-O-phenylisourea 

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.

Method for production of 4-methyl-5-(2-aminoethyl)-thiomethyl)-imidazole

4-Methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole can be effectively produced by causing 4-methylimidazole or a salt thereof to react with at least one member selected from the group consisting of (a) a formaldehyde adduct of cysteamine, (b) 2-aminoethanethiol sulfuric acid and formaldehyde or a formaldehyde oligomer, and (c) thiazolidine or a salt thereof, in the presence of a mineral acid, removing a portion of reaction liquid out of the reaction system while maintaining molar concentration of 4-methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole in the reaction system not exceeding 70 mol % based on total mol numbers of 4-methylimidazole and 4-methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole, then separating a liquid containing 4-methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole from the removed portion of reaction liquid, and recycling the remainder into the reaction system.

Process for producing 1-hydroxymethylimidazoles

1-Hydroxymethylimidazoles which are unsubstituted or alkyl-substituted in the 2-position, their manufacture and their use as chemical intermediates, e.g. for other imidazole derivatives or for the drug cimetidine.