2-Iodomelatonin

2-Iodomelatonin
Identifiers
	IUPAC name N-[2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl]acetamide;
CAS Number	93515-00-5 ;
PubChem CID	115348;
IUPHAR/BPS	1343;
DrugBank	DB08190;
ChemSpider	103191;
UNII	2Q5TZ5754A;
ChEBI	CHEBI:109558;
ChEMBL	ChEMBL289233;
CompTox Dashboard (EPA)	DTXSID30239462 ;
Chemical and physical data
Formula	C13H15IN2O2
Molar mass	358.179 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)NCCC1=C(NC2=C1C=C(C=C2)OC)I;
	InChI 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); Key:FJDDSMSDZHURBJ-UHFFFAOYSA-N;

2-Iodomelatonin is a melatonin analog used as a radiolabelled ligand for the melatonin receptors, MT₁, MT₂, and MT₃. It acts as a full agonist at both MT₁ and MT₂ receptors.^[1]

References

^ Audinot V, Mailliet F, Lahaye-Brasseur C, Bonnaud A, Le Gall A, Amossé C, Dromaint S, Rodriguez M, Nagel N, Galizzi JP, Malpaux B, Guillaumet G, Lesieur D, Lefoulon F, Renard P, Delagrange P, Boutin JA (June 2003). "New selective ligands of human cloned melatonin MT₁ and MT₂ receptors". Naunyn-Schmiedeberg's Arch Pharmacol. 367 (6): 553–61. doi:10.1007/s00210-003-0751-2. PMID 12764576. S2CID 20279702.

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[1] Audinot V, Mailliet F, Lahaye-Brasseur C, Bonnaud A, Le Gall A, Amossé C, Dromaint S, Rodriguez M, Nagel N, Galizzi JP, Malpaux B, Guillaumet G, Lesieur D, Lefoulon F, Renard P, Delagrange P, Boutin JA (June 2003). "New selective ligands of human cloned melatonin MT₁ and MT₂ receptors". Naunyn-Schmiedeberg's Arch Pharmacol. 367 (6): 553–61. doi:10.1007/s00210-003-0751-2. PMID 12764576. S2CID 20279702.

[1]

v t e Melatonin receptor modulators
MT₁Tooltip Melatonin receptor 1	Agonists: 2-Iodomelatonin 6-Hydroxymelatonin Agomelatine Fabomotizole (afobazole) GR-196,429 Melatonin N-Acetylserotonin (normelatonin) Piromelatine Ramelteon Tasimelteon TIK-301 (LY-156,735) Antagonists: Luzindole
MT₂Tooltip Melatonin receptor 2	Agonists: 2-Iodomelatonin 6-Hydroxymelatonin Agomelatine GR-196,429 Melatonin N-Acetylserotonin (normelatonin) Piromelatine Ramelteon Tasimelteon TIK-301 (LY-156,735) Antagonists: Luzindole
Unsorted	Agonists: 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin 8-M-PDOT AMMTC GR-135,531 (of MT₃Tooltip melatonin receptor 1C) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin S-24268 S-25150 Antagonists: 4-P-ADOT 4-P-PDOT DH-97 N-Acetyltryptamine (of MT₃) Prazosin (of MT₃) S-20928 S-22153 S-24601 S-25567 S-26131
See also: Receptor/signaling modulators Adrenergics Dopaminergics Serotonergics Monoamine metabolism modulators

Identifiers

IUPAC name N-[2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl]acetamide
CAS Number	93515-00-5^Y
PubChem CID	115348
IUPHAR/BPS	1343
DrugBank	DB08190
ChemSpider	103191
UNII	2Q5TZ5754A
ChEBI	CHEBI:109558
ChEMBL	ChEMBL289233
CompTox Dashboard (EPA)	DTXSID30239462
Chemical and physical data
Formula	C₁₃H₁₅IN₂O₂
Molar mass	358.179 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)NCCC1=C(NC2=C1C=C(C=C2)OC)I
InChI 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) Key:FJDDSMSDZHURBJ-UHFFFAOYSA-N

2-Iodomelatonin

References

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