[2-(1H-imidazol-4-yl)ethyl](methyl)amine dihydrochloride

• ChemBase ID: 153845
• Molecular Formular: C6H13Cl2N3
• Molecular Mass: 198.09352
• Monoisotopic Mass: 197.04865279
• SMILES: CNCCc1c[nH]cn1.Cl.Cl
• Canonical SMILES: CNCCc1nc[nH]c1.Cl.Cl
• InChI: InChI=1S/C6H11N3.2ClH/c1-7-3-2-6-4-8-5-9-6;;/h4-5,7H,2-3H2,1H3,(H,8,9);2*1H
• InChIKey: AYUQICXJAMPXPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(1H-imidazol-4-yl)ethyl](methyl)amine dihydrochloride
• IUPAC Traditional name: [2-(1H-imidazol-4-yl)ethyl](methyl)amine dihydrochloride
• Synonyms: N-Methyl-1H-imidazole-4-ethanamine dihydrochloride; NAMH dihydrochloride; Nα-Methylhistamine dihydrochloride

Database IDs

• CAS Number: 16503-22-3
• MDL Number: MFCD00134838
• PubChem SID: 162247984; 24724503
• PubChem CID: 16078977

CALCULATED PROPERTIES

• Acid pKa: 14.454073
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -4.064952
• LogD (pH = 7.4): -2.6713803
• Log P: -0.26839074
• Molar Refractivity: 36.438 cm^3
• Polarizability: 14.113825 Å^3
• Polar Surface Area: 40.71 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: (The product is pure based on elemental analysis results, NMR and MS spectra.)
• Empirical Formula (Hill Notation): C6H11N3 · 2HCl

DETAILS

Sigma Aldrich - H5914

Biochem/physiol Actions
Production of N-alpha-methyl-histamine (NAMH), a histamine H(3) receptor (H3R) agonist, is promoted in Helicobacter pylori infected human gastric mucosa. NAMH acts directly on histamine H(2) receptors (H2Rs) in animals to stimulate acid secretion and to be a H2R agonist. NAMH dose dependently stimulated cAMP productions in CHO-H2R cells. This production was inhibited by famotidine but not by thioperamide. Control CHO cells were unresponsive to either histamine or NAMH. In addition, the effect of NAMH, in terms of cAMP production in CHO-H2R cells, was more potent than that of histamine-that is, with a lower EC50 concentration and higher maximal cAMP production. Both NAMH and histamine, but not R-alpha-methyl-histamine, effectively inhibited [(3)H] tiotidine binding to CHO-H2R cells. These results confirm that NAMH, which is produced in the gastric mucosa by H pylori, is a potent H2R agonist as well as a H3R agonist.