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melatonin

File:Melatonin.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ180912· pop 73· linked from 1,555 articles

Also known as MLT, N-[2-(5-methoxyindol-3-yl)ethyl]acetamide, 5-methoxy-N-acetyltryptamine, Melovine, {N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} Acetamide, N-(2-(5-Methoxyindol-3-yl)ethyl)-Acetamide, N-Acetyl-5-methoxy-tryptamine, N-[2-(5-Methoxyindol-3-yl)ethyl]-Acetamide

Melatonin, an indoleamine, is a natural compound produced by various organisms, including bacteria and eukaryotes. Its discovery in 1958 by Aaron B. Lerner and colleagues stemmed from the isolation of a substance from the pineal gland of cows that could induce skin lightening in common frogs. This compound was later identified as a hormone secreted in the brain during the night, playing a crucial role in regulating the sleep-wake cycle, also known as the circadian rhythm, in vertebrates.

OverviewAI-generated

Melatonin is a chemical compound with the formula C₁₃H₁₆N₂O₂. Its IUPAC name is N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide. The substance has a mass of 232.121 and a weight of 232.28. It carries a charge of 0 and features two hydrogen bond donors and two hydrogen bond acceptors. The calculated xlogp value is 0.8, while the topological polar surface area (TPSA) is 54.1.

The defined daily dose for melatonin is 2.0. The compound is associated with a PubMed query count of 37218. It is referenced by 1,555 other encyclopedia articles.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C13H16N2O2
Molecular weight
232.28 g/mol
IUPAC name
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
SMILES
CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC
InChIKey
DRLFMBDRBRZALE-UHFFFAOYSA-N
XLogP
0.8
Polar surface area
54.1 Ų
H-bond donors
2
H-bond acceptors
2
Formal charge
0

via PubChem

Research

37,218 papers

via PubMed

~25 min read

Encyclopedic overview

29 sections
Contents
  • Biological activity
  • Biological functions
  • Circadian rhythm
  • Immune system
  • Weight regulation
  • Biochemistry
  • Biosynthesis
  • Mechanism
  • Regulation
  • Metabolism
  • Measurement
  • Use as a medication and supplement
  • Insomnia
  • Circadian rhythm sleep disorders
  • REM sleep behavior disorder
  • Dementia
  • Available forms
  • History
  • Discovery
  • Etymology
  • Occurrence
  • Animals and Humans
  • Plants
  • Fungi
  • Bacteria
  • Archaea
  • Food products
  • References
  • External links

Melatonin, an indoleamine, is a natural compound produced by various organisms, including bacteria and eukaryotes. Its discovery in 1958 by Aaron B. Lerner and colleagues stemmed from the isolation of a substance from the pineal gland of cows that could induce skin lightening in common frogs. This compound was later identified as a hormone secreted in the brain during the night, playing a crucial role in regulating the sleep-wake cycle, also known as the circadian rhythm, in vertebrates.

In vertebrates, melatonin's functions extend to synchronizing sleep-wake cycles, encompassing sleep-wake timing and blood pressure regulation, as well as controlling seasonal rhythmicity (circannual cycle), which includes reproduction, fattening, molting, and hibernation. Its effects are mediated through the activation of melatonin receptors and its role as an antioxidant. In plants and bacteria, it serves as a defense mechanism against oxidative stress, indicating its evolutionary significance. Mitochondria, key organelles, are the main producers of melatonin, underscoring its "ancient origins" and its fundamental role in protecting the earliest cells from reactive oxygen species.

Excerpted from Wikipedia’s “melatonin” article, available under the CC BY-SA 4.0 licence.

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