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
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
Melatonin administration prevents the nephrotoxicity induced by gentamicin.
2000 Apr
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
Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in rats.
2001
Melatonin as a sedation substitute for diagnostic procedures: MRI and EEG.
2001 Feb
Effect of exogenous melatonin on vascular reactivity and nitric oxide in postmenopausal women: role of hormone replacement therapy.
2001 Feb
Coexistence of zinc and iron augmented oxidative injuries in the nigrostriatal dopaminergic system of SD rats.
2001 Feb 1
An hPer2 phosphorylation site mutation in familial advanced sleep phase syndrome.
2001 Feb 9
Human melatonin regulation is not mediated by the three cone photopic visual system.
2001 Jan
Transition from dim to bright light in the morning induces an immediate elevation of cortisol levels.
2001 Jan
Superior cervical ganglionectomy leads to dampening of amplitude of temperature rhythm in rats.
2001 Jan
A test of the coincidence and duration models of melatonin action in Siberian hamsters. II. The effects of 4- and 8-hr melatonin infusions on testicular development of pinealectomized juvenile Siberian hamsters (Phodopus sungorus).
2001 Jan
Melatonin reduces dinitrobenzene sulfonic acid-induced colitis.
2001 Jan
Comparative analysis of reproductive cycles in female Persian gazelle (Gazella subgutturosa subgutturosa) (Central Asia) and sand gazelle (Gazella subgutturosa marica) (Arabian Peninsula).
2001 Jan
Circadian time of morning light administration and therapeutic response in winter depression.
2001 Jan
Melatonin in psychiatric disorders: a review on the melatonin involvement in psychiatry.
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
Effects of melatonin, morphine and diazepam on formalin-induced nociception in mice.
2001 Jan 12
Disruption of the nocturnal testosterone rhythm by sleep fragmentation in normal men.
2001 Mar
Multiple binding sites for melatonin on Kv1.3.
2001 Mar
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
Dual effects of melatonin on barbiturate-induced narcosis in rats.
2001 Mar 16
Melatonin inhibits the expression of steroidogenic acute regulatory protein and steroidogenesis in MA-10 cells.
2001 Mar-Apr
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 [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 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 734320
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 719519
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
CFR 21 CFR 522.1350
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 541016
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 557416
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 600317
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 677519
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 77593
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LOINC 78992-5
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LOINC 12721-7
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 888822
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
WHO-ATC N05CH01
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
DSLD 517 (Number of products:895)
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LOINC 49725-5
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 734420
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 551916
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LOINC 27060-3
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
WHO-VATC QN05CH01
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
NCI_THESAURUS C2315
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 680719
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
WIKIPEDIA TiHKAL
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LIVERTOX NBK548519
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LOINC 18183-4
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 391313
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 845921
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 644918
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 181203
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 816621
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LOINC 11055-1
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 628518
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
EMA ASSESSMENT REPORTS CICARDIN (AUTHORIZED: SLEEP INITIATION AND MAINTENANCE DISORDERS)
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 552016
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
LOINC 11056-9
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
FDA ORPHAN DRUG 704519
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID1022421
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
NCI_THESAURUS
C632
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
RXCUI
6711
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY RxNorm
DRUG BANK
DB01065
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
FDA UNII
JL5DK93RCL
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
NSC
56423
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
WIKIPEDIA
MELATONIN
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
PUBCHEM
896
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
IUPHAR
224
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
HSDB
7509
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
LACTMED
Melatonin
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
NSC
113928
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
CHEBI
31279
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
CAS
73-31-4
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
MERCK INDEX
M7154
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY Merck Index
RS_ITEM_NUM
1380105
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
ChEMBL
CHEMBL45
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
CHEBI
16796
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
DAILYMED
JL5DK93RCL
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
MESH
D008550
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
DRUG CENTRAL
1672
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
EVMPD
SUB14496MIG
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-797-7
Created by admin on Fri Dec 16 15:48:51 UTC 2022 , Edited by admin on Fri Dec 16 15:48:51 UTC 2022
PRIMARY