Melatonin

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 °C
Pharmacology
Pharmacokinetics:
20–50 minutes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Not to be confused with melanin. For the album, see Melatonin (album).
This article is about melatonin as a hormone. For its role as a supplement and medication, see Melatonin as a medication and supplement.

Melatonin is a natural compound, specifically an indoleamine, produced by and found in different organisms including bacteria and eukaryotes. It was discovered by Aaron B. Lerner and colleagues in 1958 as a substance of the pineal gland from cows that could induce skin lightening in common frogs. It was subsequently discovered as a hormone released in the brain at night which controls the sleep–wake cycle in vertebrates.

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. Many of its effects are through activation of the melatonin receptors, while others are due to its role as an antioxidant. Its primary function is to defend against oxidative stress in plants and bacteria. Mitochondria are the main cell organelles that produce the antioxidant melatonin, which indicates that melatonin is an "ancient molecule" that primarily provided the earliest cells protection from the destructive actions of oxygen.

In addition to its role as a natural hormone and antioxidant, melatonin is used as a dietary supplement and medication in the treatment of sleep disorders such as insomnia and circadian rhythm sleep disorders.

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