2-Phenylmelatonin

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Description: Potent melatonin agonist
Chemical Name: N-[2-(5-Methoxy-2-phenylindol-3-yl)ethyl]acetamide
Purity: ≥98% (HPLC)
Datasheet
Citations (3)
Reviews (1)
Literature (1)

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.

Select a batch to recalculate based on the batch molecular weight:
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

Certificate of Analysis / Product Datasheet
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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:

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

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


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

PMID: 31019306

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!

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