Chemical Component Summary

NameN-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
SynonymsMelatonin
IdentifiersN-[2-(5-methoxy-1H-indol-3-yl)ethyl]ethanamide
FormulaC13 H16 N2 O2
Molecular Weight232.278
TypeNON-POLYMER
Isomeric SMILESCC(=O)NCCc1c[nH]c2c1cc(cc2)OC
InChIInChI=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)
InChIKeyDRLFMBDRBRZALE-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count33
Chiral Atom Count0
Bond Count34
Aromatic Bond Count10

Drug Info: DrugBank

DrugBank IDDB01065 
NameMelatonin
Groups
  • vet_approved
  • nutraceutical
  • approved
DescriptionMelatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature. Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.
Synonyms
  • N-[2-(5-methoxyindol-3-yl)ethyl]acetamide
  • Melatonin
  • N-Acetyl-5-methoxytryptamine
  • Mélatonine
  • 5-methoxy-N-acetyltryptamine
Brand Names
  • Essential Oil
  • Amerix Melatonin
  • Melatonin Rapid Release Gelcaps 10 mg
  • Medi-doze Rx Sleep Aid
  • Melatonin Neurim
IndicationUsed orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders.
Categories
  • Amines
  • Antioxidants
  • Biogenic Amines
  • Biogenic Monoamines
  • Biological Factors
ATC-CodeN05CH01
CAS number73-31-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Melatonin receptor type 1AMQGNGSALPNASQPVLRGDGARPSWLASALACVLIFTIVVDILGNLLVIL...unknownagonist
Melatonin receptor type 1BMSENGSFANCCEAGGWAVRPGWSGAGSARPSRTPRPPWVAPALSAVLIVT...unknownagonist
Estrogen receptor alphaMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownantagonist
Nuclear receptor ROR-betaMCENQLKTKADATAQIEVIPCKICGDKSSGIHYGVITCEGCKGFFRRSQQ...unknownagonist
CalmodulinMADQLTEEQIAEFKEAFSLFDKDGDGTITTKELGTVMRSLGQNPTEAELQ...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL45
PubChem 896
ChEMBL CHEMBL45
ChEBI CHEBI:16796
CCDC/CSD MELATN01, ROHWIX, MELATN04, ROHWIX02, XOSWIN, MELATN02, MELATN, MELATN03
COD 7218717