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

Molecular Formula C13H16N2O2
Molecular Weight 232.2788
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
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
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
Melatonin's gastroprotective and antistress roles involve both central and peripheral effects.
2001 Feb
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
Low ambient temperature accelerates short-day responses in Siberian hamsters by altering responsiveness to melatonin.
2001 Feb
Effect of exogenous melatonin on vascular reactivity and nitric oxide in postmenopausal women: role of hormone replacement therapy.
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
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
The critical stage of pinealectomy surgery after which scoliosis is produced in young chickens.
2001 Feb 1
Pineal modulation of thymus and immune function in a seasonally breeding tropical rodent, Funambulus pennanti.
2001 Feb 1
Coexistence of zinc and iron augmented oxidative injuries in the nigrostriatal dopaminergic system of SD rats.
2001 Feb 1
Human melatonin suppression by light: a case for scotopic efficiency.
2001 Feb 16
Melatonin secretion after surgery.
2001 Feb 17
Rhythms of the pineal N-acetyltransferase mRNA and melatonin concentrations during embryonic and post-embryonic development in chicken.
2001 Feb 2
An hPer2 phosphorylation site mutation in familial advanced sleep phase syndrome.
2001 Feb 9
Melatonin in medically ill patients with insomnia: a double-blind, placebo-controlled study.
2001 Jan
Interaction between the adrenal and the pineal gland in chronic experimental inflammation induced by BCG in mice.
2001 Jan
[Melatonin: is there a rationale for the clinical use of this hormone in sleep therapy?].
2001 Jan
[Drug for the treatment of sleep disorders--review].
2001 Jan
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
Diminished melatonin secretion in the elderly caused by insufficient environmental illumination.
2001 Jan
Circadian phase resetting in older people by ocular bright light exposure.
2001 Jan
Superior cervical ganglionectomy leads to dampening of amplitude of temperature rhythm in rats.
2001 Jan
Bright light therapy and melatonin in motor restless behaviour in dementia: a placebo-controlled study.
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
Lack of changes in serum prolactin, FSH, TSH, and estradiol after melatonin treatment in doses that improve sleep and reduce benzodiazepine consumption in sleep-disturbed, middle-aged, and elderly patients.
2001 Jan
Melatonin reduces dinitrobenzene sulfonic acid-induced colitis.
2001 Jan
Inhibition of androgen-sensitive LNCaP prostate cancer growth in vivo by melatonin: association of antiproliferative action of the pineal hormone with mt1 receptor protein expression.
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
Effects of melatonin, morphine and diazepam on formalin-induced nociception in mice.
2001 Jan 12
Effects by doxorubicin on the myocardium are mediated by oxygen free radicals.
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 inhibits Arg-vasopressin release via MT(2) receptor in the suprachiasmatic nucleus-slice culture of rats.
2001 Jan 19
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
A randomized, double-blind, placebo-controlled crossover study of the effect of exogenous melatonin on delayed sleep phase syndrome.
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
The immunotherapeutic potential of melatonin.
2001 Mar
Effect of melatonin on oxidative status of rat brain, liver and kidney tissues under constant light exposure.
2001 Mar
Multiple binding sites for melatonin on Kv1.3.
2001 Mar
Photoresponsive Fischer 344 Rats are reproductively inhibited by melatonin and differ in 2-[125I] lodomelatonin binding from nonphotoresponsive Sprague-Dawley rats.
2001 Mar
Phenolamine-dependent adenylyl cyclase activation in Drosophila Schneider 2 cells.
2001 Mar 15
Dual effects of melatonin on barbiturate-induced narcosis in rats.
2001 Mar 16
Tissue-specific abolition of Per1 expression in the pars tuberalis by pinealectomy in the Syrian hamster.
2001 Mar 5
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:29:56 UTC 2021
Edited
by admin
on Fri Jun 25 21:29:56 UTC 2021
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 [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
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
DSLD 517 (Number of products:895)
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 49725-5
Created by admin on Fri Jun 25 21:29:56 UTC 2021 , Edited by admin on Fri Jun 25 21:29:56 UTC 2021
FDA ORPHAN DRUG 734420
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 551916
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 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
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
Related Record Type Details
ACTIVE MOIETY