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Melatonin

Hormone released by the pineal gland / From Wikipedia, the free encyclopedia

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Melatonin
Melatonin.svg
Melatonin_molecule_ball.png
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 Edit this at Wikidata
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[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 compound, specifically an indoleamine, produced by and found in different organisms including bacteria and eukaryotes.[4] It was discovered by Aaron B. Lerner and colleagues in 1958 as a substance of the pineal gland from cow 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.[2][5]

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.[6] Many of its effects are through activation of the melatonin receptors, while others are due to its role as an antioxidant.[7][8][9] Its primary function is to defend against oxidative stress in plants[10] and bacteria. Mitochondria are the main cell organelles that produce the antioxidant melatonin,[11] which indicates that melatonin is an "ancient molecule" that primarily provided the earliest cells protection from the destructive actions of oxygen.[12][13]

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.