MedKoo Cat#: 462451 | Name: 2-Iodomelatonin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

2-Iodomelatonin is a synthetic iodinated analog of melatonin that acts as a high-affinity agonist at melatonin receptors MT₁ and MT₂, with enhanced receptor binding compared to native melatonin. It exhibits bioactivity in regulating circadian rhythms, sleep, and thermoregulation, making it useful in neuroendocrine and chronobiology research. Its mechanism of action involves activation of G-protein-coupled melatonin receptors in the suprachiasmatic nucleus (SCN), leading to downstream modulation of cyclic AMP and other intracellular signaling pathways.

Chemical Structure

2-Iodomelatonin
2-Iodomelatonin
CAS#93515-00-5

Theoretical Analysis

MedKoo Cat#: 462451

Name: 2-Iodomelatonin

CAS#: 93515-00-5

Chemical Formula: C13H15IN2O2

Exact Mass: 358.0178

Molecular Weight: 358.18

Elemental Analysis: C, 43.59; H, 4.22; I, 35.43; N, 7.82; O, 8.93

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 550.00 2 Weeks
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Related CAS #
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Synonym
2-Iodomelatonin
IUPAC/Chemical Name
N-(2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl)acetamide
InChi Key
FJDDSMSDZHURBJ-UHFFFAOYSA-N
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)
SMILES Code
CC(NCCC1=C(I)NC2=C1C=C(OC)C=C2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 358.18 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.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Bedini A, Elisi GM, Fanini F, Retini M, Scalvini L, Pasquini S, Contri C, Varani K, Spadoni G, Mor M, Vincenzi F, Rivara S. Binding and unbinding of potent melatonin receptor ligands: Mechanistic simulations and experimental evidence. J Pineal Res. 2024 Mar;76(2):e12941. doi: 10.1111/jpi.12941. PMID: 38606814. 2: Calamini B, Ferry G, Boutin JA. Melatonin Binding to Human NQO2 by Isothermal Titration Calorimetry. Methods Mol Biol. 2022;2550:305-314. doi: 10.1007/978-1-0716-2593-4_32. PMID: 36180701. 3: Wang Q, Lu Q, Guo Q, Teng M, Gong Q, Li X, Du Y, Liu Z, Tao Y. Structural basis of the ligand binding and signaling mechanism of melatonin receptors. Nat Commun. 2022 Jan 24;13(1):454. doi: 10.1038/s41467-022-28111-3. PMID: 35075127; PMCID: PMC8786939. 4: Elisi GM, Scalvini L, Lodola A, Mor M, Rivara S. Free-Energy Simulations Support a Lipophilic Binding Route for Melatonin Receptors. J Chem Inf Model. 2022 Jan 10;62(1):210-222. doi: 10.1021/acs.jcim.1c01183. Epub 2021 Dec 21. PMID: 34932329; PMCID: PMC8757440. 5: Ciani E, Fontaine R, Maugars G, Mizrahi N, Mayer I, Levavi-Sivan B, Weltzien FA. Melatonin receptors in Atlantic salmon stimulate cAMP levels in heterologous cell lines and show season-dependent daily variations in pituitary expression levels. J Pineal Res. 2019 Oct;67(3):e12590. doi: 10.1111/jpi.12590. Epub 2019 Jun 23. PMID: 31169933. 6: Nishiyama K, Hirai K. In vitro comparison of duration of action of melatonin agonists on melatonin MT1 receptor: possible link between duration of action and dissociation rate from receptor. Eur J Pharmacol. 2015 Jun 15;757:42-52. doi: 10.1016/j.ejphar.2015.03.009. Epub 2015 Mar 20. PMID: 25797281. 7: Corthell JT, Olcese J, Trombley PQ. Melatonin in the mammalian olfactory bulb. Neuroscience. 2014 Mar 7;261:74-84. doi: 10.1016/j.neuroscience.2013.12.033. Epub 2013 Dec 21. PMID: 24365461; PMCID: PMC3939688. 8: Feng NY, Bass AH. Melatonin action in a midbrain vocal-acoustic network. J Exp Biol. 2014 Apr 1;217(Pt 7):1046-57. doi: 10.1242/jeb.096669. Epub 2013 Nov 21. PMID: 24265429; PMCID: PMC3966919. 9: Adamah-Biassi EB, Zhang Y, Jung H, Vissapragada S, Miller RJ, Dubocovich Ml. Distribution of MT1 melatonin receptor promoter-driven RFP expression in the brains of BAC C3H/HeN transgenic mice. J Histochem Cytochem. 2014 Jan;62(1):70-84. doi: 10.1369/0022155413507453. Epub 2013 Sep 18. PMID: 24051358; PMCID: PMC3873804. 10: Legros C, Matthey U, Grelak T, Pedragona-Moreau S, Hassler W, Yous S, Thomas E, Suzenet F, Folleas B, Lefoulon F, Berthelot P, Caignard DH, Guillaumet G, Delagrange P, Brayer JL, Nosjean O, Boutin JA. New radioligands for describing the molecular pharmacology of MT1 and MT2 melatonin receptors. Int J Mol Sci. 2013 Apr 25;14(5):8948-62. doi: 10.3390/ijms14058948. PMID: 23698757; PMCID: PMC3676766. 11: Lau WW, Ng JK, Lee MM, Chan AS, Wong YH. Interleukin-6 autocrine signaling mediates melatonin MT(1/2) receptor-induced STAT3 Tyr(705) phosphorylation. J Pineal Res. 2012 May;52(4):477-89. doi: 10.1111/j.1600-079X.2011.00965.x. Epub 2011 Sep 28. PMID: 21954831. 12: Pegan SD, Sturdy M, Ferry G, Delagrange P, Boutin JA, Mesecar AD. X-ray structural studies of quinone reductase 2 nanomolar range inhibitors. Protein Sci. 2011 Jul;20(7):1182-95. doi: 10.1002/pro.647. Epub 2011 May 23. PMID: 21538647; PMCID: PMC3149192. 13: Shiu SY, Pang B, Tam CW, Yao KM. Signal transduction of receptor-mediated antiproliferative action of melatonin on human prostate epithelial cells involves dual activation of Gα(s) and Gα(q) proteins. J Pineal Res. 2010 Oct;49(3):301-11. doi: 10.1111/j.1600-079X.2010.00795.x. Epub 2010 Aug 1. PMID: 20695976. 14: Ishii H, Sato S, Yin C, Sakuma Y, Kato M. Cetrorelix, a gonadotropin- releasing hormone antagonist, induces the expression of melatonin receptor 1a in the gonadotropin-releasing hormone neuronal cell line GT1-7. Neuroendocrinology. 2009;90(3):251-9. doi: 10.1159/000231993. Epub 2009 Jul 30. PMID: 19641296. 15: Velarde E, Alonso-Gómez AL, Azpeleta C, Isorna E, Delgado MJ. Melatonin attenuates the acetylcholine-induced contraction in isolated intestine of a teleost fish. J Comp Physiol B. 2009 Nov;179(8):951-9. doi: 10.1007/s00360-009-0373-1. Epub 2009 Jun 20. PMID: 19543897. 16: Ishii H, Tanaka N, Kobayashi M, Kato M, Sakuma Y. Gene structures, biochemical characterization and distribution of rat melatonin receptors. J Physiol Sci. 2009 Jan;59(1):37-47. doi: 10.1007/s12576-008-0003-9. Epub 2008 Dec 6. PMID: 19340560; PMCID: PMC10717452. 17: Fujinoki M. Melatonin-enhanced hyperactivation of hamster sperm. Reproduction. 2008 Nov;136(5):533-41. doi: 10.1530/REP-08-0202. Epub 2008 Aug 20. PMID: 18715981. 18: Tam CW, Chan KW, Liu VW, Pang B, Yao KM, Shiu SY. Melatonin as a negative mitogenic hormonal regulator of human prostate epithelial cell growth: potential mechanisms and clinical significance. J Pineal Res. 2008 Nov;45(4):403-12. doi: 10.1111/j.1600-079X.2008.00608.x. Epub 2008 Jul 10. PMID: 18637986. 19: Audinot V, Bonnaud A, Grandcolas L, Rodriguez M, Nagel N, Galizzi JP, Balik A, Messager S, Hazlerigg DG, Barrett P, Delagrange P, Boutin JA. Molecular cloning and pharmacological characterization of rat melatonin MT1 and MT2 receptors. Biochem Pharmacol. 2008 May 15;75(10):2007-19. doi: 10.1016/j.bcp.2008.02.022. Epub 2008 Mar 4. PMID: 18384758. 20: Gavrilov SS, Kulinskiĭ VI. [5-hydroxytryptamine and 5-methoxytryptamine increase tolerance to global cerebral ischemia]. Eksp Klin Farmakol. 2007 Nov- Dec;70(6):17-8. Russian. PMID: 18318189.