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Quick facts: Names, Identifiers, Properties, Pharmacology...
Melatonin
Names
IUPAC name
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Other names
5-Methoxy-N-acetyltryptamine; N-Acetyl-5-methoxytryptamine; NSC-113928
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.725
EC Number
  • 200-797-7
KEGG
  • InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
    Key: DRLFMBDRBRZALE-UHFFFAOYSA-N
  • CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC
Properties
C13H16N2O2
Molar mass 232.281 g/mol
Melting point 117
Pharmacology
Pharmacokinetics:
20–50 minutes[1][2][3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Melatonin is a natural product found in plants and animals. It is primarily known in animals as a hormone released by the pineal gland in the brain at night, and has long been associated with control of the sleep–wake cycle.[2][4]

In vertebrates, melatonin is involved in synchronizing circadian rhythms, including sleep–wake timing and blood pressure regulation, and in control of seasonal rhythmicity including reproduction, fattening, moulting and hibernation.[5] Many of its effects are through activation of the melatonin receptors, while others are due to its role as an antioxidant.[6][7][8] In plants, it functions to defend against oxidative stress.[9] It is also present in various foods.[10]

Melatonin was discovered in 1958.[2]

In addition to its role as a natural hormone, melatonin is used as a dietary supplement and medication in the treatment of sleep disorders such as insomnia and circadian rhythm sleep disorders; for information on melatonin as a supplement and medication, see the melatonin (supplement/medication) article.