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
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)
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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Ultrastructural confirmation of neuronal protection by melatonin against the neurotoxin 6-hydroxydopamine cell damage. | 1999 Feb 13 |
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Aspects of melatonin manufacturing and requirements for a reliable active component. | 1999 Jan-Apr |
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Ototoxicity caused by aminoglycosides is ameliorated by melatonin without interfering with the antibiotic capacity of the drugs. | 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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Role of heme oxygenase-1 in the regulation of manganese superoxide dismutase gene expression in oxidatively-challenged astroglia. | 2000 Oct |
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The antioxidative potential of melatonin in the skin. | 2001 |
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Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in 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 aging on the intrinsic circadian period of totally blind humans. | 2001 Feb |
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Chronic exposure to ELF magnetic fields during night sleep with electric sheet: effects on diurnal melatonin rhythms in men. | 2001 Feb |
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The influence of 1.2 microT, 60 Hz magnetic fields on melatonin- and tamoxifen-induced inhibition of MCF-7 cell growth. | 2001 Feb |
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The influence of long-term exposure of mice to randomly varied power frequency magnetic fields on their nocturnal melatonin secretion patterns. | 2001 Feb |
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Circadian regulation of phospholipid metabolism in retinal photoreceptors and ganglion cells. | 2001 Feb |
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Plasma melatonin concentration before and during testosterone replacement in Klinefelter's syndrome: relation to hepatic indolamine metabolism and sympathoadrenal activity. | 2001 Feb |
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Pineal modulation of thymus and immune function in a seasonally breeding tropical rodent, Funambulus pennanti. | 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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Risk of breast cancer among Norwegian women with visual impairment. | 2001 Feb 2 |
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[Melatonin: is there a rationale for the clinical use of this hormone in sleep therapy?]. | 2001 Jan |
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Human melatonin regulation is not mediated by the three cone photopic visual system. | 2001 Jan |
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Circadian phase resetting in older people by ocular bright light exposure. | 2001 Jan |
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Bright light therapy and melatonin in motor restless behaviour in dementia: a placebo-controlled study. | 2001 Jan |
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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 |
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Seasonal alterations in circadian melatonin rhythms of the European wild boar and domestic gilt. | 2001 Jan |
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Changes of serum melatonin level and its relationship to feto-placental unit during pregnancy. | 2001 Jan |
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Melatonin protects against 6-OHDA-induced neurotoxicity in rats: a role for mitochondrial complex I activity. | 2001 Jan |
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Melatonin production in healthy infants: evidence for seasonal variations. | 2001 Jan |
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Vitamin D resistance in RAS-transformed keratinocytes: mechanism and reversal strategies. | 2001 Jan |
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Circadian variation in O6-alkylguanine-DNA alkyltransferase activity in circulating blood mononuclear cells of healthy human subjects. | 2001 Jan 1 |
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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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Melatonin counteracts potentiation by homocysteine of KCL-induced vasoconstriction in human umbilical artery: relation to calcium influx. | 2001 Jan 26 |
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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 |
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Disruption of the nocturnal testosterone rhythm by sleep fragmentation in normal men. | 2001 Mar |
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Circadian rhythms of women with fibromyalgia. | 2001 Mar |
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Effect of melatonin on oxidative status of rat brain, liver and kidney tissues under constant light exposure. | 2001 Mar |
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Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. | 2001 Mar |
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.
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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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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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LIVERTOX |
594
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LOINC |
18183-4
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FDA ORPHAN DRUG |
391313
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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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73-31-4
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C632
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6711
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DB01065
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JL5DK93RCL
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MELATONIN
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896
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224
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7509
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Melatonin
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1380105
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73-31-4
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M7154
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CHEMBL45
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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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ACTIVE MOIETY
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