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
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)
Molecular Formula | C13H16N2O2 |
Molecular Weight | 232.2783 |
Charge | 0 |
Count |
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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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P48039 Gene ID: 4543.0 Gene Symbol: MTNR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19966183 |
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Target ID: P49286 Gene ID: 4544.0 Gene Symbol: MTNR1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19449447 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Zinc accumulation in adriamycin-induced cardiomyopathy in rats: effects of melatonin, a cardioprotective antioxidant. | 1999 May |
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Mercury induces cell cytotoxicity and oxidative stress and increases beta-amyloid secretion and tau phosphorylation in SHSY5Y neuroblastoma cells. | 2000 Jan |
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Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors. | 2000 Mar |
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Melatonin suppresses iron-induced neurodegeneration in rat brain. | 2000 Mar 15 |
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Cardiovascular effects of melatonin in hypertensive patients well controlled by nifedipine: a 24-hour study. | 2000 May |
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Synthesis of phenalene and acenaphthene derivatives as new conformationally restricted ligands for melatonin receptors. | 2000 Nov 2 |
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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 |
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Effects of melatonin in perimenopausal and menopausal women: a randomized and placebo controlled study. | 2001 Feb |
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Effects of bilateral ganglionectomy and melatonin replacement on seasonal rhythm of testicular activity in Zembra Island wild rabbits (Oryctolagus cuniculus). | 2001 Feb |
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Effects of aging on the intrinsic circadian period of totally blind humans. | 2001 Feb |
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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 |
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Photoperiodic regulation of prolactin gene expression in the Syrian hamster by a pars tuberalis-derived factor. | 2001 Feb |
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Coexistence of zinc and iron augmented oxidative injuries in the nigrostriatal dopaminergic system of SD rats. | 2001 Feb 1 |
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Rhythms of the pineal N-acetyltransferase mRNA and melatonin concentrations during embryonic and post-embryonic development in chicken. | 2001 Feb 2 |
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Human melatonin regulation is not mediated by the three cone photopic visual system. | 2001 Jan |
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Melatonin and its analogs potentiate the nifedipine-sensitive high-voltage-activated calcium current in the chick embryonic heart cells. | 2001 Jan |
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Circadian time of morning light administration and therapeutic response in winter depression. | 2001 Jan |
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Melatonin potentiates contractile responses to serotonin in isolated porcine coronary arteries. | 2001 Jan |
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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 |
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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 |
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Effect of melatonin on circadian rhythm, locomotor activity and body temperature in the intact house sparrow, Japanese quail and owl. | 2001 Jan 19 |
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Melatonin counteracts potentiation by homocysteine of KCL-induced vasoconstriction in human umbilical artery: relation to calcium influx. | 2001 Jan 26 |
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Effects of vehicles and enhancers on transdermal delivery of melatonin. | 2001 Jan 5 |
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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
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01161108
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28475125
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
Edited
Fri Dec 15 14:58:41 GMT 2023
by
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on
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Record UNII |
JL5DK93RCL
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
melatonin
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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
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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
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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
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FDA ORPHAN DRUG |
644918
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FDA ORPHAN DRUG |
181203
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FDA ORPHAN DRUG |
816621
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LOINC |
11055-1
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FDA ORPHAN DRUG |
628518
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EMA ASSESSMENT REPORTS |
CICARDIN (AUTHORIZED: SLEEP INITIATION AND MAINTENANCE DISORDERS)
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FDA ORPHAN DRUG |
552016
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LOINC |
11056-9
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FDA ORPHAN DRUG |
704519
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DTXSID1022421
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C632
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6711
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DB01065
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JL5DK93RCL
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56423
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MELATONIN
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896
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7509
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Melatonin
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113928
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31279
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m7154
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1380105
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CHEMBL45
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16796
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JL5DK93RCL
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D008550
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1672
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SUB14496MIG
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200-797-7
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> AGONIST |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
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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.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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