เมลาโทนิน

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.

In the Vinony graph

Within Vinony's link graph, เมลาโทนิน is referenced by 1,555 other articles, and connects out to tryptamines, controlled release and serotonin.

It sits within the topics 5-Methoxytryptamines, ECHA InfoCard ID from Wikidata and Melatonin.

Its subject is documented across 72 Wikipedia language editions.

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 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2007
Admin. routes: oral
Indications: sunburn, substance withdrawal syndrome, aortic aneurysm, metabolic syndrome

via ChEMBL · EBI