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Submit Review(R)-(-)-α-Methylhistamine dihydrobromide
Description: Potent, standard H3 agonist
Chemical Name: (R)-(-)-α-Methyl-1H-imidazole-4-ethanamine dihydrobromide
Purity: ≥98% (HPLC)
Biological Activity
(R)-(-)-α-Methylhistamine dihydrobromide is a very potent, high affinity H3 agonist (KD = 50.3 nM) that displays > 200-fold selectivity over H4 receptors. Inhibits H3-mediated histamine synthesis and release in the CNS and stimulates H4-mediated eosinophil shape change (EC50 = 66 nM).
S-enantiomer also available.
Technical Data
| M. Wt | 287 |
| Formula | C6H11N3.2HBr |
| Storage | Desiccate at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 868698-49-1 |
| PubChem ID | 45037031 |
| InChI Key | RWHNAAABSGVRDT-ZJIMSODOSA-N |
| Smiles | N[C@H](C)CC1=CNC=N1.Br.Br |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 28.7 | 100 |
Preparing Stock Solutions
The following data is based on the product molecular weight 287. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.48 mL | 17.42 mL | 34.84 mL |
| 5 mM | 0.7 mL | 3.48 mL | 6.97 mL |
| 10 mM | 0.35 mL | 1.74 mL | 3.48 mL |
| 50 mM | 0.07 mL | 0.35 mL | 0.7 mL |
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Product Datasheets
References
References are publications that support the biological activity of the product.
Buckland et al (2003) Histamine induces cytoskeletal changes in human eosinophils via the H4 receptor. Br.J.Pharmacol. 140 1117 PMID: 14530216
Hew et al (1990) Characterization of histamine-H3 receptors in guinea pig ileum with H3-selective ligands. Br.J.Pharmacol. 101 621 PMID: 1963802
Oishi et al (1989) Effects of histamine H3-agonist (R)-α-methylhistamine and the antagonist thioperamide on histamine modulation in the mouse and rat brain. J.Neurochem. 52 1388 PMID: 2540269
Schwartz et al (1990) A third histamine receptor subtype - characterization, localization and functions of the H3-receptor. Agents Actions 30 13 PMID: 1695431
Shahid et al (2009) Histamine, histamine receptors, and their role in immunomodulation: An updated systematic review. Open Immunol.J. 2 9
If you know of a relevant reference for (R)-(-)-α-Methylhistamine dihydrobromide, please let us know.
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Keywords: (R)-(-)-alpha-Methylhistamine dihydrobromide, (R)-(-)-alpha-Methylhistamine dihydrobromide supplier, Potent, H3, agonists, Receptors, Histamine, histaminergic, (R)-(-)-alpha-Methylhistamine, dihydrobromide, 0569, Tocris Bioscience
4 Citations for (R)-(-)-α-Methylhistamine dihydrobromide
Citations are publications that use Tocris products. Selected citations for (R)-(-)-α-Methylhistamine dihydrobromide include:
Holden et al (2007) Potentiation of NF-κB-dependent transcription and inflammatory mediator release by histamine in human airway epithelial cells. FASEB J 152 891 PMID: 17891168
Rapanelli et al (2016) The Histamine H3 Receptor Differentially Modulates Mitogen-activated Protein Kinase (MAPK) and Akt Signaling in Striatonigral and Striatopallidal Neurons. J Biol Chem. 291 21042 PMID: 27510032
Kim et al (2013) Effects of histamine on cultured interstitial cells of cajal in murine small intestine. Korean J Physiol Pharmacol 17 149 PMID: 23626477
Spaethling et al (2014) Serotonergic neuron regulation informed by in vivo single-cell transcriptomics. J Clin Invest 28 771 PMID: 24192459
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Histamine Receptors Scientific Review
Written by Iwan de Esch and Rob Leurs, this review provides a synopsis of the different histamine receptor subtypes and the ligands that act upon them; compounds available from Tocris are listed.
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