U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H16N2O2
Molecular Weight 232.2788
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELATONIN

SMILES

CC(=NCCc1c[nH]c2ccc(cc12)OC)O

InChI

InChIKey=DRLFMBDRBRZALE-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Melatonin (5-methoxy N-acetyltryptamine) is a hormone synthesized and released from the pineal gland at night, which acts on specific high affinity G-protein coupled receptors to regulate various aspects of physiology and behaviour, including circadian and seasonal responses, and some retinal, cardiovascular and immunological functions. Melatonin is also made synthetically and available without a prescription as an over-the-counter (OTC) dietary supplement in the U.S. Melatonin supplementation has many uses, however, it has been widely studied for treatment of jet lag and sleep disorders. Parents may consider using melatonin to help their child who has a trouble falling asleep. A medical professional should always evaluate insomnia or other sleeping disorders in children. Additionally, melatonin has been shown to protect against oxidative stress in various, highly divergent experimental systems. There are many reasons for its remarkable protective potential. In mammals, melatonin binds to a number of receptor subtypes including high-affinity (MT1 and MT2) and low-affinity (MT3, nuclear orphan receptors) binding sites, which are distributed throughout the central nervous system and periphery.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P48039
Gene ID: 4543.0
Gene Symbol: MTNR1A
Target Organism: Homo sapiens (Human)
Target ID: P49286
Gene ID: 4544.0
Gene Symbol: MTNR1B
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ultrastructural confirmation of neuronal protection by melatonin against the neurotoxin 6-hydroxydopamine cell damage.
1999 Feb 13
Aspects of melatonin manufacturing and requirements for a reliable active component.
1999 Jan-Apr
Ototoxicity caused by aminoglycosides is ameliorated by melatonin without interfering with the antibiotic capacity of the drugs.
2000 Jan
Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors.
2000 Mar
Melatonin suppresses iron-induced neurodegeneration in rat brain.
2000 Mar 15
Role of heme oxygenase-1 in the regulation of manganese superoxide dismutase gene expression in oxidatively-challenged astroglia.
2000 Oct
The antioxidative potential of melatonin in the skin.
2001
Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in rats.
2001
Effects of melatonin in perimenopausal and menopausal women: a randomized and placebo controlled study.
2001 Feb
Effects of aging on the intrinsic circadian period of totally blind humans.
2001 Feb
Chronic exposure to ELF magnetic fields during night sleep with electric sheet: effects on diurnal melatonin rhythms in men.
2001 Feb
The influence of 1.2 microT, 60 Hz magnetic fields on melatonin- and tamoxifen-induced inhibition of MCF-7 cell growth.
2001 Feb
The influence of long-term exposure of mice to randomly varied power frequency magnetic fields on their nocturnal melatonin secretion patterns.
2001 Feb
Circadian regulation of phospholipid metabolism in retinal photoreceptors and ganglion cells.
2001 Feb
Plasma melatonin concentration before and during testosterone replacement in Klinefelter's syndrome: relation to hepatic indolamine metabolism and sympathoadrenal activity.
2001 Feb
Pineal modulation of thymus and immune function in a seasonally breeding tropical rodent, Funambulus pennanti.
2001 Feb 1
Rhythms of the pineal N-acetyltransferase mRNA and melatonin concentrations during embryonic and post-embryonic development in chicken.
2001 Feb 2
Risk of breast cancer among Norwegian women with visual impairment.
2001 Feb 2
[Melatonin: is there a rationale for the clinical use of this hormone in sleep therapy?].
2001 Jan
Human melatonin regulation is not mediated by the three cone photopic visual system.
2001 Jan
Circadian phase resetting in older people by ocular bright light exposure.
2001 Jan
Bright light therapy and melatonin in motor restless behaviour in dementia: a placebo-controlled study.
2001 Jan
Absolute configuration of N-[(-)-2-(7-methoxy-1,2,3,3-tetrahydro-1-naphthyl)ethyl]cyclopropylcarboxamide, a highly potent and selective melatonin analogue.
2001 Jan
Seasonal alterations in circadian melatonin rhythms of the European wild boar and domestic gilt.
2001 Jan
Changes of serum melatonin level and its relationship to feto-placental unit during pregnancy.
2001 Jan
Melatonin protects against 6-OHDA-induced neurotoxicity in rats: a role for mitochondrial complex I activity.
2001 Jan
Melatonin production in healthy infants: evidence for seasonal variations.
2001 Jan
Vitamin D resistance in RAS-transformed keratinocytes: mechanism and reversal strategies.
2001 Jan
Circadian variation in O6-alkylguanine-DNA alkyltransferase activity in circulating blood mononuclear cells of healthy human subjects.
2001 Jan 1
Direct separation of the stereoisomers of methoxytetrahydronaphthalene derivatives, new agonist and antagonist ligands for melatonin receptors, by liquid chromatography on cellulose chiral stationary phases.
2001 Jan 12
Melatonin counteracts potentiation by homocysteine of KCL-induced vasoconstriction in human umbilical artery: relation to calcium influx.
2001 Jan 26
The effect of short intermittent light exposures on the melatonin circadian rhythm and NMU-induced breast cancer in female F344/N rats.
2001 Jan-Feb
Disruption of the nocturnal testosterone rhythm by sleep fragmentation in normal men.
2001 Mar
Circadian rhythms of women with fibromyalgia.
2001 Mar
Effect of melatonin on oxidative status of rat brain, liver and kidney tissues under constant light exposure.
2001 Mar
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
Patents

Sample Use Guides

Fast Release Melatonin (FR MLT): 3mg capsules of melatonin will be used. The dose of FR MLT will be 3 mg for children less than or equal to 20 kg, and 6 mg for children greater than 20 kg. The study medication will be given one hour before bedtime, once daily. Drug: Timed Release Melatonin (TR MLT): 3 mg capsules will be used. The dose of TR MLT will be will be 3 mg for children less than or equal to 20 kg, and 6 mg for children greater than 20 kg. The study medication will be given one hour before bedtime, once daily.
Route of Administration: Oral
It was observed that 10-7 M melatonin was considered an optimum concentration and significantly promoted the in vitro development of murine microinjected pronuclear embryos, as indicated by the increased blastocyst rate, hatching blastocyst rate and blastocyst cell number. When these blastocysts were implanted into recipient mice, the pregnancy rate and birth rate were significantly higher than those of the microinjected control, respectively. Mechanistic studies revealed that melatonin treatment reduced reactive oxygen species (ROS) production and cellular apoptosis during in vitro embryo development and improved the quality of the blastocysts. The implantation of quality-improved blastocysts led to elevated pregnancy and birth rates. In conclusion, the results revealed that the anti-oxidative and anti-apoptotic activities of melatonin improved the quality of microinjected pronuclear embryos and subsequently increased both the efficiency of embryo implantation and the birth rate of the pups. Therefore, the melatonin supplementation may provide a novel alternative method for generating large numbers of transgenic mice and this method can probably be used in human-assisted reproduction and genome editing.
Name Type Language
MELATONIN
DSC   EMA EPAR   GREEN BOOK   HSDB   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
MELATONIN [EMA EPAR]
Common Name English
ACETAMIDE, N-(2-(5-METHOXYINDOL-3-YL)ETHYL)-
Systematic Name English
REGULIN
Brand Name English
MELATONIN [USP-RS]
Common Name English
MELATONIN [INCI]
Common Name English
MELATONIN [WHO-DD]
Common Name English
MELATONINE
Common Name English
NSC-113928
Code English
MELATONIN [HSDB]
Common Name English
MELATONIN [DSC]
Common Name English
BCI-049
Code English
MELATONIN [MI]
Common Name English
MELATONIN [GREEN BOOK]
Common Name English
J5.258B
Code English
ACETAMIDE, N-(2-(5-METHOXY-1H-INDOL-3-YL)ETHYL)-
Systematic Name English
MELATOL
Brand Name English
MELOVINE
Brand Name English
NSC-56423
Code English
CIRCADIN
Brand Name English
5-METHOXY N-ACETYL-TRYPTAMINE
Common Name English
MELATONIN [MART.]
Common Name English
MELATONIN [VANDF]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug melatonin
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 734320
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 719519
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
CFR 21 CFR 522.1350
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 541016
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 557416
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 600317
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 677519
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 77593
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
LOINC 78992-5
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
LOINC 12721-7
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
WHO-ATC N05CH01
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DSLD 517 (Number of products:895)
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LOINC 49725-5
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FDA ORPHAN DRUG 734420
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FDA ORPHAN DRUG 551916
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LOINC 27060-3
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
WHO-VATC QN05CH01
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
NCI_THESAURUS C2315
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 680719
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
LIVERTOX 594
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
LOINC 18183-4
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 391313
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 644918
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 181203
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 816621
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
LOINC 11055-1
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 628518
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
EMA ASSESSMENT REPORTS CICARDIN (AUTHORIZED: SLEEP INITIATION AND MAINTENANCE DISORDERS)
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 552016
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
LOINC 11056-9
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 704519
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
Code System Code Type Description
EPA CompTox
73-31-4
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
NCI_THESAURUS
C632
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
RXCUI
6711
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB01065
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
FDA UNII
JL5DK93RCL
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
WIKIPEDIA
MELATONIN
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
PUBCHEM
896
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
IUPHAR
224
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
HSDB
7509
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
LACTMED
Melatonin
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
USP_CATALOG
1380105
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY USP-RS
CAS
73-31-4
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
MERCK INDEX
M7154
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL45
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
MESH
D008550
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
DRUG CENTRAL
1672
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
EVMPD
SUB14496MIG
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-797-7
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
PRIMARY