A MT receptor mixed partial agonist and antagonist
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2-Phenylmelatonin

Item No. 35004

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(5-methoxy-2-phenyl-1H-indol-3-yl)ethyl]-acetamide
CAS Number
151889-03-1
Synonyms
  • N-acetyl-5-methoxy-2-phenyl Tryptamine
Molecular Formula
C19H20N2O2
Formula Weight
308.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 100 mMEthanol: 100 mM
SMILES
O=C(C)NCCC1=C(C2=CC=CC=C2)NC3=C1C=C(C=C3)OC
InChi Code
InChI=1S/C19H20N2O2/c1-13(22)20-11-10-16-17-12-15(23-2)8-9-18(17)21-19(16)14-6-4-3-5-7-14/h3-9,12,21H,10-11H2,1-2H3,(H,20,22)
InChi Key
OFCLARYYBGKCHN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $107

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    10 mg

    $204

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    Product Description

    2-Phenylmelatonin is a melatonin 1 (MT1) and MT2 receptor mixed partial agonist and antagonist.1,2,3 It selectively binds to MT1 and MT2 receptors (Kis = 0.02 and 0.09 nM, respectively, in HEK293 cells expressing the human receptors) over the MT3 receptor (Ki = 33 nM in hamster brain membranes).1 2-Phenylmelatonin induces [35S]GTPγS binding to NIH3T3 cell membranes expressing the human MT2 receptor (EC50 = 0.058 nM).2 It induces contractions (EC50 = 0.5 nM) and inhibits melatonin-induced contractions in isolated guinea pig proximal colon strips when used at a concentration of 0.1 nM.3 2-Phenylmelatonin reduces intraocular pressure in rabbits (pD2 = 8.7).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nosjean, O., Nicolas, J.P., Klupsch, F., et al. Comparative pharmacological studies of melatonin receptors: MT1, MT2 and MT3/QR2. Tissue distribution of MT3/QR2. Biochem. Pharmacol. 61(11), 1369-1379 (2001).

    2. Nonno, R., Pannacci, M., Lucini, V., et al. Ligand efficacy and potency at recombinant human MT2 melatonin receptors: Evidence for agonist activity of some mt1-antagonists. Brit. J. Pharmacol. 127(5), 1288-1294 (2016).

    3. Santagostino-Barbone, M.G., Masoero, E., Spelta, V., et al. 2-Phenylmelatonin: A partial agonist at enteric melatonin receptors. Pharmacol. Toxicol. 87(4), 156-160 (2000).

    4. Pintor, J., Peláez, T., Hoyle, C.H.V., et al. Ocular hypotensive effects of melatonin receptor agonists in the rabbit: Further evidence for an MT3 receptor. Br. J. Pharmacol. 138(5), 831-836 (2003).