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73-31-4 molecular structure
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N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

ChemBase ID: 936
Molecular Formular: C13H16N2O2
Molecular Mass: 232.27834
Monoisotopic Mass: 232.12117776
SMILES and InChIs

SMILES:
O(c1cc2c(CCNC(=O)C)c[nH]c2cc1)C
Canonical SMILES:
COc1ccc2c(c1)c(CCNC(=O)C)c[nH]2
InChI:
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)
InChIKey:
DRLFMBDRBRZALE-UHFFFAOYSA-N

Cite this record

CBID:936 http://www.chembase.cn/molecule-936.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
IUPAC Traditional name
melatonin
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Brand Name
Circadin
MT6
Mela-T
Melatol
Melatonex
Melatonine
Melovine
Night Rest
Revital Melatonin
Melatonin
Nature'S Harmony
Rx Balance
Sleep Right
Vivitas
Synonyms
N-acetyl-5-methoxytryptamine
MEL
MLT
Pineal Hormone
Melatonin
N-ACETYL-5-METHOXYTRYPTAMINE
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide
5-Methoxy-N-acetyltryptamine
Circadin
Melatol
Melatonine
Melovine
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamide
NSC 113928
NSC 56423
Regulin
Melatonin
SITS
Disodium 4-acetamido-4'-isothiocyanato-stilben-2,2'-disulfonate
4-ACETAMIDO-4'-ISOTHIOCYANATOSTILBENE-2,2'-DISULFONIC ACID DISODIUM SALT
Melatonex
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
N -[2-(5-Methoxy-1 H -indol-3-yl)ethyl]acetamide
N -Acetyl-5-methoxytryptamine
N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide
N-乙酰基-5-甲氧基色胺
褪黑素
CAS Number
73-31-4
51023-76-8
EC Number
200-797-7
256-919-4
MDL Number
MFCD00005655
Beilstein Number
205542
PubChem SID
46509101
24278103
160964399
PubChem CID
896
CHEBI ID
16796
ATC CODE
N05CH01
CHEMBL
45
Chemspider ID
872
DrugBank ID
DB01065
IUPHAR ligand ID
224
KEGG ID
D08170
Unique Ingredient Identifier
JL5DK93RCL
Wikipedia Title
Melatonin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.795497  H Acceptors
H Donor LogD (pH = 5.5) 1.1476127 
LogD (pH = 7.4) 1.1476128  Log P 1.1476128 
Molar Refractivity 66.2799 cm3 Polarizability 26.624952 Å3
Polar Surface Area 54.12 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.42  LOG S -3.21 
Solubility (Water) 1.43e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
ethanol: soluble8 mg/mL expand Show data source
H2O: soluble0.1 mg/mL expand Show data source
Methanol expand Show data source
Apperance
off-white powder expand Show data source
Off-White Powder expand Show data source
Melting Point
116.5-118 °C(lit.) expand Show data source
116-118°C expand Show data source
117-120 °C expand Show data source
117-120°C expand Show data source
Hydrophobicity(logP)
1.6 expand Show data source
Storage Condition
0°C expand Show data source
0°C, Desiccate, Protect from light expand Show data source
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
AC5955000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
In humans: orally, as capsules, tablets or liquid, sublingually, or as transdermal patches. In lab animals: also injection. expand Show data source
Bioavailability
30 – 50% expand Show data source
Excretion
Urine expand Show data source
Half Life
35 to 50 minutes expand Show data source
Metabolism
Hepatic via CYP1A2 mediated 6-hydroxylation expand Show data source
Legal Status
OTC (US) expand Show data source
S4 (Australia) expand Show data source
Gene Information
human ... MTNR1A(4543), MTNR1B(4544), NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846) expand Show data source
Mechanism of Action
Dopamine antagonist expand Show data source
Prolactin antagonist expand Show data source
Purity
≥98% (TLC) expand Show data source
≥99.0% (TLC) expand Show data source
≥99.5% expand Show data source
95+% expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Biological Source
Isol. from bovine pineal glands expand Show data source
Application(s)
May influence circadian rhythms in humans expand Show data source
Potent effects on the control of seasonal reproduction in mammals expand Show data source
Product of tryptophan metabolism by the pineal gland expand Show data source
Synthesis and secretion subject to photoperiodic control expand Show data source
Tumour-inhibiting props. and role in immune system under investigation expand Show data source
Empirical Formula (Hill Notation)
C13H16N2O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05210417 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02102254 external link
Crystalline
A hormone of the pineal gland.
MP Biomedicals - 02100015 external link
Disodium Salt
Note: A non-penetrating fluorescent marker for erythrocyte membranes which acts as a potent inhibitor of anion transport.
DrugBank - DB01065 external link
Item Information
Drug Groups approved; nutraceutical
Description Melatonin 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.
Indication Used 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.
Pharmacology Melatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag.
MT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions
Toxicity

Generally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established.


Oral, rat: LD50 ≥3200 mg/kg


Affected Organisms
Humans and other mammals
Biotransformation Hepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine).
Absorption The absorption and bioavailability of melatonin varies widely.
Half Life 35 to 50 minutes
Protein Binding n/a
References
Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [Pubmed]
Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. [Pubmed]
Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. [Pubmed]
Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. [Pubmed]
Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. Epub 2008 Jan 10. [Pubmed]
Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. [Pubmed]
External Links
Wikipedia
PDRhealth
Drugs.com
DrugBank - DB08189 external link
Drug information: experimental
Selleck Chemicals - S1204 external link
Research Area: Endocrinology
Biological Activity:
Melatonin is a hormone produced in the brain by the pineal gland from the amino acid tryptophan. The synthesis and release of melatonin are stimulated by darkness and suppressed by light, suggesting the involvement of melatonin in circadian rhythm and regulation of diverse body functions. Tryptophan is converted to serotonin and finally converted to melatonin which is an Indole. [1]Synthetic melatonin supplements have been used for a variety of medical conditions, most notably for jet-lag and disturbances of sleep. Melatonin possesses antioxidant activity, and many of its proposed therapeutic or preventive uses are based on this property. [2]
Sigma Aldrich - M5250 external link
Caution
Solutions are light sensitive and subject to oxidation.
包装
1, 5, 10 g in glass bottle
250 mg in glass bottle
Biochem/physiol Actions
Hormone; mediates photoperiodicity in mammals; inhibits cerebellar nitric oxide synthetase; peroxynitrite scavenger. Melatonin has complex effects on apoptotic pathways, inhibiting apoptosis in immune cells and neurons but enhancing apoptotic cell death of cancer cells. Inhibits proliferation/metastasis of breast cancer cells by inhibiting estrogen receptor action.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M5250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - M215000 external link
Hormone; mediates photoperiodicity in mammals; inhibits cerebellar nitric oxide synthetase; peroxynitrite scavenger. Melatonin has complex effects on apoptotic pathways, inhibiting apoptosis in immune cells and neurons but enhancing apoptotic cell death o

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. Pubmed
  • • Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. Pubmed
  • • Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. Pubmed
  • • Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. Pubmed
  • • Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. Epub 2008 Jan 10. Pubmed
  • • Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. Pubmed
  • • http://en.wikipedia.org/wiki/Melatonin
  • • Barchas, et al.: Nature, 214, 919 (1967)
  • • Glass, J.D., et al.: Science, 214, 821 (1967)
  • • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 663A
  • • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 677A, (ir)
  • • Adlerova, I. et al., Coll. Czech. Chem. Comm., 1960, 25, 784; CA, 54, 13095f
  • • Szmuszkovicz, J. et al., J.O.C., 1960, 25, 857, (synth, uv)
  • • Quarles, W.G. et al., Acta Cryst. B, 1974, 30, 99, (cryst struct)
  • • Mattox, S.E. et al., Biomed. Mass Spectrom., 1975, 2, 272, (synth, ms)
  • • Minneman, K.P. et al., Life Sci., 1975, 17, 1189, (rev, pharmacol)
  • • Arendt, J., Clin. Endocrinol. (Oxford), 1988, 29, 205, (Melatonin, rev)
  • • Neville, S. et al., J. Pineal Res., 1989, 6, 73, (mutagenicity)
  • • Dubcovich, M.L., Adv. Pineal Res., 1991, 5, 343-349, (Melatonin, pharmacol)
  • • Reiter, R.J., Endocr. Rev., 1991, 12, 151, (Melatonin, rev)
  • • Guerrero, J.M. et al., Endocr. Rev., 1992, 18, 91, (Melatonin)
  • • Vivien-Roels, B. et al., Experientia, 1993, 49, 642, (rev, Melatonin)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1385, (Melatonin)
  • • Weniger, B. et al., Planta Med., 1995, 61, 569-570, (isol, deriv)
  • • Marais, W. et al., Synth. Commun., 1998, 28, 3681-3691, (Melatonin)
  • • Hwang, K.-J. et al., Synth. Commun., 1999, 29, 2099-2104, (Melatonin, synth, pmr)
  • • Somei, M. et al., Heterocycles, 2000, 53, 1725-1736, (Melatonin, synth)
  • • Somei, M. et al., Chem. Pharm. Bull., 2001, 49, 87-96, (synth, deriv, Melatonin)
  • • Amat, M. et al., Synthesis, 2001, 267-275, (Melatonin)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCB350; MFT000; MFS400
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