2-Phenylmelatonin

Name: 2-Phenylmelatonin
Brand: Tocris Bioscience
SKU: 0680
Rating: 5 (1 reviews)

Tocris Bioscience a Bio-Techne Brand

Catalog # 0680

Citations (3)

(1)

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Key Product Details

Description:	Potent melatonin agonist
Chemical Name:	N-[2-(5-Methoxy-2-phenylindol-3-yl)ethyl]acetamide
Purity:	≥98% (HPLC)
Molecular Weight:	308.38

View Full Technical Details for 2-Phenylmelatonin

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 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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References for 2-Phenylmelatonin

References are publications that support the biological activity of the product.

Nonno Ligand efficacy and potency at recombinant human MT₂ melatonin receptors: evidence for agonist activity of some mt₁-antagonists. Br.J.Pharmacol. 1999 PMID: 10455277
Nonno Pharmacological characterization of the human melatonin Mel_1a receptor following stable transfection into NIH3T3 cells. Br.J.Pharmacol. 1998 PMID: 9647472
Spadoni 2-Substituted 5-methoxy-N-acetyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity. J.Med.Chem. 1993 PMID: 8258829

Citations for 2-Phenylmelatonin (3)

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Citations are publications that use Bio-Techne 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

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Customer Reviews for 2-Phenylmelatonin (1)

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Highly recommended for in vitro stabilization and crystallization of melatonin receptors

Name: Anonymous

Species: Human

Assay Type: In Vitro

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

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Product Documents for 2-Phenylmelatonin

COA

Certificate of Analysis

To download a Certificate of Analysis, please select a batch below.