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Submit ReviewCimetidine
Description: H2 antagonist, I1 agonist
Chemical Name: N-Cyano-N'-methyl-N''-[2-[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]guanidine
Purity: ≥99% (HPLC)
Biological Activity for Cimetidine
Cimetidine is a widely used H2 histamine antagonist which has more recently been described as an inverse agonist. Also a potent I1 imidazoline binding site ligand.
Compound Libraries for Cimetidine
Cimetidine is also offered as part of the Tocriscreen FDA-Approved Drugs. Find out more about compound libraries available from Tocris.
Technical Data for Cimetidine
| M. Wt | 252.34 |
| Formula | C10H16N6S |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 51481-61-9 |
| PubChem ID | 2756 |
| InChI Key | AQIXAKUUQRKLND-UHFFFAOYSA-N |
| Smiles | CN\C(NCCSCC1=C(C)NC=N1)=N\C#N |
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 for Cimetidine
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 50 | ||
| DMSO | 25.23 | 100 |
Preparing Stock Solutions for Cimetidine
The following data is based on the product molecular weight 252.34. 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 | 3.96 mL | 19.81 mL | 39.63 mL |
| 5 mM | 0.79 mL | 3.96 mL | 7.93 mL |
| 10 mM | 0.4 mL | 1.98 mL | 3.96 mL |
| 50 mM | 0.08 mL | 0.4 mL | 0.79 mL |
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Product Datasheets for Cimetidine
Certificate of Analysis is currently unavailable on-line.
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References for Cimetidine
References are publications that support the biological activity of the product.
Hill (1990) Distribution, properties and functional characteristics of three classes of histamine receptor. Pharmacol.Rev. 42 45 PMID: 2164693
Smit et al (1996) Inverse agonism of histamine H2 antagonists accounts for upregulation of spontaneously active receptors. Proc.Natl.Acad.Sci.U.S.A. 93 6802 PMID: 8692899
Tsoli et al (1995) The imidazoline I1 receptor agonist, moxonidine, inhibits Ins secretion from isolated rat islets of langerhans. Eur.J.Pharmacol. 284 199 PMID: 8549627
Ernsberger et al (1992) A second generation of centrally acting antihypertensive agents act on putative I1-imidazoline receptors. J.Cardiovasc.Pharmacol. 20 S1
If you know of a relevant reference for Cimetidine, please let us know.
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Keywords: Cimetidine, Cimetidine supplier, I1, agonists, histamine, H2, antagonists, inverse, Imidazoline, Receptors, histaminergic, Histamine, 0902, Tocris Bioscience
8 Citations for Cimetidine
Citations are publications that use Tocris products. Selected citations for Cimetidine include:
Wang et al (2014) Roles of histamine on the expression of aldehyde dehydrogenase 1 in endometrioid adenocarcinoma cell line. J Neurosci 3 1126 PMID: 25045085
Connelly et al (2009) The histamine H4 receptor is functionally expressed on neurons in the mammalian CNS. Br J Pharmacol 157 55 PMID: 19413571
Kurtz et al (2014) Involvement of H1 and H2 receptors and soluble guanylate cyclase in histamine-induced relaxation of rat mesenteric collecting lymphatics. Microcirculation 21 593 PMID: 24702851
Francis et al (2012) Inhibition of histidine decarboxylase ablates the autocrine tumorigenic effects of histamine in human cholangiocarcinoma. Gut 61 753 PMID: 21873469
Femenia et al (2015) Hippocampal-Dependent Antidepressant Action of the H3 Receptor Antagonist Clobenpropit in a Rat Model of Depression. Int J Neuropsychopharmacol 18 PMID: 25762718
Hough et al (2007) CC12, a high-affinity ligand for [3H]cimetidine binding, is an improgan antagonist. Neuropharmacology 52 1244 PMID: 17336343
Strait et al (2006) IgG-blocking antibodies inhibit IgE-mediated anaphylaxis in vivo through both antigen interception and Fc gamma RIIb cross-linking. J Clin Invest 116 833 PMID: 16498503
André et al (2006) Enhancing functional production of G protein-coupled receptors in Pichia pastoris to levels required for structural studies via a single expression screen. Protein Sci 15 1115 PMID: 16597836
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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.