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Submit Review2-Phenylmelatonin
Description: Potent melatonin agonist
Chemical Name: N-[2-(5-Methoxy-2-phenylindol-3-yl)ethyl]acetamide
Purity: ≥98% (HPLC)
Biological Activity for 2-Phenylmelatonin
2-Phenylmelatonin is a highly potent melatonin agonist; displays higher affinity and greater potency than melatonin itself. The EC50 values for G protein activation in MT1 and MT2-transfected cells are 65 and 58 pM respectively.
Technical Data for 2-Phenylmelatonin
| M. Wt | 308.38 |
| Formula | C19H20N2O2 |
| Storage | Desiccate at +4°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 151889-03-1 |
| PubChem ID | 4018512 |
| InChI Key | OFCLARYYBGKCHN-UHFFFAOYSA-N |
| Smiles | COC1=CC=C2NC(=C(CCNC(C)=O)C2=C1)C1=CC=CC=C1 |
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 2-Phenylmelatonin
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 30.84 | 100 | |
| DMSO | 30.84 | 100 |
Preparing Stock Solutions for 2-Phenylmelatonin
The following data is based on the product molecular weight 308.38. 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 | 3.24 mL | 16.21 mL | 32.43 mL |
| 5 mM | 0.65 mL | 3.24 mL | 6.49 mL |
| 10 mM | 0.32 mL | 1.62 mL | 3.24 mL |
| 50 mM | 0.06 mL | 0.32 mL | 0.65 mL |
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Product Datasheets for 2-Phenylmelatonin
References for 2-Phenylmelatonin
References are publications that support the biological activity of the product.
Nonno et al (1998) Pharmacological characterization of the human melatonin Mel1a receptor following stable transfection into NIH3T3 cells. Br.J.Pharmacol. 124 485 PMID: 9647472
Nonno et al (1999) Ligand efficacy and potency at recombinant human MT2 melatonin receptors: evidence for agonist activity of some mt1-antagonists. Br.J.Pharmacol. 127 1288 PMID: 10455277
Spadoni et al (1993) 2-Substituted 5-methoxy-N-acetyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity. J.Med.Chem. 36 4069 PMID: 8258829
If you know of a relevant reference for 2-Phenylmelatonin, please let us know.
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Keywords: 2-Phenylmelatonin, 2-Phenylmelatonin supplier, Potent, melatonin, agonists, MT, Receptors, Melatonin, (MT), 0680, Tocris Bioscience
3 Citations for 2-Phenylmelatonin
Citations are publications that use Tocris products. Selected citations for 2-Phenylmelatonin include:
Stauch et al (2019) Structural basis of ligand recognition at the human MT1 melatonin receptor Nature 569 284 PMID: 31019306
Johansson et al (2019) XFEL structures of the human MT2 melatonin receptor reveal the basis of subtype selectivity. Nature 569 289 PMID: 31019305
Akoume et al (2019) A Differential Hypofunctionality of Gαi Proteins Occurs in Adolescent Idiopathic Scoliosis and Correlates with the Risk of Disease Progression. Sci Rep 9 10074 PMID: 31296888
Do you know of a great paper that uses 2-Phenylmelatonin from Tocris? Please let us know.
Reviews for 2-Phenylmelatonin
Average Rating: 5 (Based on 1 Review.)
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Highly recommended for in vitro stabilization and crystallization of melatonin receptors.
By
Anonymous on 10/11/2022
Assay Type: In Vitro
Species: Human
After trying many other melatonin receptor ligands, this has become our gold standard for stabilizing MT1 and MT2 melatonin GPCRs for in vitro studies. Given its high potency, relatively low micromolar concentrations are sufficient to achieve the desired effect. We found that it sufficiently stabilizes MTRs for crystallization purposes. Additionally, in cell based GPCR activity assays, it is able to achieve an efficacy as high as, or higher, than the endogenous ligand melatonin. Highly recommended if you value maximum stabilization and/or efficacy
Dissolves well in DMSO