H5914

N^α-Methylhistamine dihydrochloride

solid

• Synonym(s): N-Methyl-1H-imidazole-4-ethanamine dihydrochloride, NAMH dihydrochloride
• Empirical Formula (Hill Notation): C₆H₁₁N₃ · 2HCl
• CAS Number: 16503-22-3
• Molecular Weight: 198.09
• MDL number: MFCD00134838
• UNSPSC Code: 12352116
• PubChem Substance ID: 24724503
• NACRES: NA.77

Properties

• form: solid
• color: white
• solubility: H₂O: >20 mg/mL
• storage temp.: 2-8°C
• SMILES string: Cl[H].Cl[H].CNCCc1c[nH]cn1
• 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
• InChI key: AYUQICXJAMPXPF-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Nα-Methylhistamine dihydrochloride helps in removing or decreasing the headache in migraine prophylaxis. It is highly effective than histamine in inducing cyclic adenosine 3′,5′-monophosphate (cAMP) synthesis.

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.

Features and Benefits

This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Quality

The product is pure based on elemental analysis results, NMR and MS spectra.

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H302,H315,H318,H335
• pcodes: P280 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 + P310
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves