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)
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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Melatonin administration prevents the nephrotoxicity induced by gentamicin. | 2000 Apr |
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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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Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in rats. | 2001 |
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Melatonin as a sedation substitute for diagnostic procedures: MRI and EEG. | 2001 Feb |
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Effect of exogenous melatonin on vascular reactivity and nitric oxide in postmenopausal women: role of hormone replacement therapy. | 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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An hPer2 phosphorylation site mutation in familial advanced sleep phase syndrome. | 2001 Feb 9 |
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Human melatonin regulation is not mediated by the three cone photopic visual system. | 2001 Jan |
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Transition from dim to bright light in the morning induces an immediate elevation of cortisol levels. | 2001 Jan |
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Superior cervical ganglionectomy leads to dampening of amplitude of temperature rhythm in rats. | 2001 Jan |
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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 |
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Melatonin reduces dinitrobenzene sulfonic acid-induced colitis. | 2001 Jan |
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Comparative analysis of reproductive cycles in female Persian gazelle (Gazella subgutturosa subgutturosa) (Central Asia) and sand gazelle (Gazella subgutturosa marica) (Arabian Peninsula). | 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 in psychiatric disorders: a review on the melatonin involvement in psychiatry. | 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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Effects of melatonin, morphine and diazepam on formalin-induced nociception in mice. | 2001 Jan 12 |
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Disruption of the nocturnal testosterone rhythm by sleep fragmentation in normal men. | 2001 Mar |
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Multiple binding sites for melatonin on Kv1.3. | 2001 Mar |
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Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. | 2001 Mar |
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Dual effects of melatonin on barbiturate-induced narcosis in rats. | 2001 Mar 16 |
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Melatonin inhibits the expression of steroidogenic acute regulatory protein and steroidogenesis in MA-10 cells. | 2001 Mar-Apr |
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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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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C632
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896
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224
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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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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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