A potent MT1 receptor agonist
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2-Iodomelatonin

Item No. 19711

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl]-acetamide
CAS Number
93515-00-5
Molecular Formula
C13H15IN2O2
Formula Weight
358.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 20 mg/ml
λmax
214, 279 nm
SMILES
COC1=CC=C(NC(I)=C2CCNC(C)=O)C2=C1
InChi Code
InChI=1S/C13H15IN2O2/c1-8(17)15-6-5-10-11-7-9(18-2)3-4-12(11)16-13(10)14/h3-4,7,16H,5-6H2,1-2H3,(H,15,17)
InChi Key
FJDDSMSDZHURBJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    5 mg

    $54

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    10 mg

    $85

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    25 mg

    $197

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    Product Description

    2-iodomelatonin is a potent agonist of melatonin receptor 1 (MT1; Ki = 28 pM) that is 5-fold selective for MT1 over MT2.1,2 It inhibits forskolin-stimulated cAMP production in CHO cells expressing human MT1 30-fold more potently than melatonin (Item No. 14427) with an EC50 value of 11 pM. 2-iodomelatonin has been used to characterize the role of MT1 in melatonin-mediated signaling.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dubocovich, M.L., Masana, M.I., Iacob, S., et al. Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor. Naunyn-Schmiedeberg's Arch. Pharmacol. 355(3), 365-375 (1997).

    2. Browning, C., Beresford, I., Fraser, N., et al. Pharmacological characterization of human recombinant melatonin mt1 and MT2 receptors. Br. J. Pharmacol. 129(5), 877-886 (2000).

    3. Cecon, E., Chen, M., Marçola, M., et al. Amyloid β peptide directly impairs pineal gland melatonin synthesis and melatonin receptor signaling through the ERK pathway. FASEB J. 29(6), 2566-2582 (2015).

    4. Adamah-Biassi, E.B., Zhang, Y., Jung, H., et al. Distribution of MT1 melatonin receptor promoter-driven RFP expression in the brains of BAC C3H/HeN transgenic mice. J. Histochem. Cytochem. 62(1), 70-84 (2014).