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H5914

Sigma-Aldrich

Nα-Methylhistamine dihydrochloride

solid

Synonym(s):

N-Methyl-1H-imidazole-4-ethanamine dihydrochloride, NAMH dihydrochloride

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About This Item

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

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

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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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N alpha methyl histamine versus propranolol in migraine prophylaxis
Millan GRO, et al.
The Canadian Journal of Neurological Sciences, 41(2), 233-238 (2014)
Noriko Hino et al.
The Journal of pharmacology and experimental therapeutics, 375(2), 276-285 (2020-08-31)
Histamine H3 receptor antagonists/inverse agonists are known to enhance the activity of histaminergic neurons in the brain, thereby promoting arousal and cognition. Here, we report the in vitro and in vivo pharmacological profiles for a newly synthesized histamine H3 receptor
Effects of N-alpha-methyl-histamine on human H2 receptors expressed in CHO cells
Saitoh T, et al.
Gut, 50(6), 786-789 (2002)

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