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

Details

Stereochemistry ACHIRAL
Molecular Formula C13H16N2O2
Molecular Weight 232.2783
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELATONIN

SMILES

COC1=CC2=C(NC=C2CCNC(C)=O)C=C1

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

Molecular Formula C13H16N2O2
Molecular Weight 232.2783
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Zinc accumulation in adriamycin-induced cardiomyopathy in rats: effects of melatonin, a cardioprotective antioxidant.
1999 May
Mercury induces cell cytotoxicity and oxidative stress and increases beta-amyloid secretion and tau phosphorylation in SHSY5Y neuroblastoma cells.
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
Cardiovascular effects of melatonin in hypertensive patients well controlled by nifedipine: a 24-hour study.
2000 May
Synthesis of phenalene and acenaphthene derivatives as new conformationally restricted ligands for melatonin receptors.
2000 Nov 2
Effects of tamoxifen and melatonin on mammary gland cancer induced by N-methyl-N-nitrosourea and by 7,12-dimethylbenz(a)anthracene, respectively, in female Sprague-Dawley rats.
2001
Effects of melatonin in perimenopausal and menopausal women: a randomized and placebo controlled study.
2001 Feb
Effects of bilateral ganglionectomy and melatonin replacement on seasonal rhythm of testicular activity in Zembra Island wild rabbits (Oryctolagus cuniculus).
2001 Feb
Effects of aging on the intrinsic circadian period of totally blind humans.
2001 Feb
Diurnal and seasonal variations in the duration and depth of the longest dives in southern elephant seals (Mirounga leonina): possible physiological and behavioural constraints.
2001 Feb
Photoperiodic regulation of prolactin gene expression in the Syrian hamster by a pars tuberalis-derived factor.
2001 Feb
Coexistence of zinc and iron augmented oxidative injuries in the nigrostriatal dopaminergic system of SD rats.
2001 Feb 1
Rhythms of the pineal N-acetyltransferase mRNA and melatonin concentrations during embryonic and post-embryonic development in chicken.
2001 Feb 2
Human melatonin regulation is not mediated by the three cone photopic visual system.
2001 Jan
Melatonin and its analogs potentiate the nifedipine-sensitive high-voltage-activated calcium current in the chick embryonic heart cells.
2001 Jan
Circadian time of morning light administration and therapeutic response in winter depression.
2001 Jan
Melatonin potentiates contractile responses to serotonin in isolated porcine coronary arteries.
2001 Jan
A single nocturnal exposure to 2-7 millitesla static magnetic fields does not inhibit the excretion of 6-sulfatoxymelatonin in healthy young men.
2001 Jan
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
Effect of melatonin on circadian rhythm, locomotor activity and body temperature in the intact house sparrow, Japanese quail and owl.
2001 Jan 19
Melatonin counteracts potentiation by homocysteine of KCL-induced vasoconstriction in human umbilical artery: relation to calcium influx.
2001 Jan 26
Effects of vehicles and enhancers on transdermal delivery of melatonin.
2001 Jan 5
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:41 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:41 GMT 2023
Record UNII
JL5DK93RCL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MELATONIN
DSC   EMA EPAR   GREEN BOOK   HSDB   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
MELATONIN [JAN]
Common 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
MELATONINE
Common Name English
NSC-113928
Code English
MELATONIN [HSDB]
Common Name English
MELATONIN [DSC]
Common Name English
BCI-049
Code English
Melatonin [WHO-DD]
Common Name 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 Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 734320
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FDA ORPHAN DRUG 719519
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CFR 21 CFR 522.1350
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FDA ORPHAN DRUG 541016
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 557416
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FDA ORPHAN DRUG 600317
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FDA ORPHAN DRUG 677519
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FDA ORPHAN DRUG 77593
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LOINC 78992-5
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LOINC 12721-7
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FDA ORPHAN DRUG 888822
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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
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WHO-VATC QN05CH01
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NCI_THESAURUS C2315
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FDA ORPHAN DRUG 680719
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WIKIPEDIA TiHKAL
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
LIVERTOX NBK548519
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LOINC 18183-4
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FDA ORPHAN DRUG 391313
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FDA ORPHAN DRUG 845921
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 644918
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 181203
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 816621
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
LOINC 11055-1
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 628518
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
EMA ASSESSMENT REPORTS CICARDIN (AUTHORIZED: SLEEP INITIATION AND MAINTENANCE DISORDERS)
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 552016
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
LOINC 11056-9
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
FDA ORPHAN DRUG 704519
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID1022421
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
NCI_THESAURUS
C632
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PRIMARY
RXCUI
6711
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PRIMARY RxNorm
DRUG BANK
DB01065
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
FDA UNII
JL5DK93RCL
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
NSC
56423
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PRIMARY
SMS_ID
100000090233
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PRIMARY
WIKIPEDIA
MELATONIN
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
PUBCHEM
896
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
IUPHAR
224
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PRIMARY
HSDB
7509
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
LACTMED
Melatonin
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PRIMARY
NSC
113928
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PRIMARY
CHEBI
31279
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PRIMARY
CAS
73-31-4
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PRIMARY
MERCK INDEX
m7154
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PRIMARY Merck Index
RS_ITEM_NUM
1380105
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PRIMARY
ChEMBL
CHEMBL45
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PRIMARY
CHEBI
16796
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PRIMARY
DAILYMED
JL5DK93RCL
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
MESH
D008550
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PRIMARY
DRUG CENTRAL
1672
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PRIMARY
EVMPD
SUB14496MIG
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PRIMARY
ECHA (EC/EINECS)
200-797-7
Created by admin on Fri Dec 15 14:58:41 GMT 2023 , Edited by admin on Fri Dec 15 14:58:41 GMT 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
METABOLITE -> PARENT
C3HOM is found to be a more potent antioxidant than melatonin or vitamin C in terms of its ability to scavenge the hydroxyl radical (HO.) and to recover oxidized horseradish peroxidase to its ground state.
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY