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M5250 Sigma

Melatonin

powder, ≥98% (TLC)

Synonym: N-Acetyl-5-methoxytryptamine

Purchase

Description

Caution

Solutions are light sensitive and subject to oxidation.

Packaging

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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.

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Mass Spectrometry Metabolite Library

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Safety & Documentation

Safety Information

WGK Germany 
2
RTECS 
AC5955000

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Melatonin as a pharmacological agent against neuronal loss in experimental models of Huntington's disease, Alzheimer's disease and parkinsonism. Reiter, R.J., et al. Ann. N. Y. Acad. Sci. 890, 471-485, (1999)

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Melatonin and cell death: differential actions on apoptosis in normal and cancer cells. Sainz, R.M., et al. Cell. Mol. Life Sci. 60, 1407-1426, (2003)

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Melatonin and mammary cancer: a short review. Sanchez-Barcelo, E.J., et al. Endocrinol. Relat. Cancer 10, 153-159, (2003)

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The protective role of endogenous melatonin in carrageenan-induced pleurisy in the rat. Cuzzocrea, S, et al. FASEB J. 13, 1930, (1999)

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The circadian timing system and reproduction in mammals. Goldman, B.D. Steroids 64, 679, (1999)

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Protection Of Rat Chromosomes By Melatonin Against Gamma Radiation-induced Damage. Assayed, M.E., and Abd El-Aty, A.M. Mol. Cell. 677, 14-20, (2009)

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Development And Validation Of A High Throughput Direct Radioimmunoassay For The Quantitative Determination Of Serum And Plasma Melatonin (N-acetyl-5-methoxytryptamine) In Mice. Welp, A., et al. J. Immunol. Methods 358, 1-8, (2010)

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The role of melatonin in the cells of the innate immunity: a review. Calvo JR, González-Yanes C, and Maldonado MD J. Pineal Res. 55(2), 103-20, (2013)

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Drastic neofunctionalization associated with evolution of the timezyme AANAT 500 Mya. Falcón J, Coon SL, Besseau L, et al. Proc. Natl. Acad. Sci. U. S. A. 111(1), 314-9, (2014)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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N-(substituted-anilinoethyl)amides: design, synthesis, and pharmacological characterization of a new class of melatonin receptor ligands. Silvia Rivara et al J. Med. Chem. 50, 6618-26, (2007)

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Manipulating melatonin in managing mood. Boyce P and Hopwood M Acta Psychiatr. Scand. Suppl. (444), 16-23, (2013)

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Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. Dolusic, E.; et al. J. Med. Chem. 54, 5320, (2011)

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A systematic review of peri-operative melatonin. Andersen LP, Werner MU, Rosenberg J, et al. Anaesthesia 69(10), 1163-71, (2014)

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Melatonin supplementation during controlled ovarian stimulation for women undergoing assisted reproductive technology: systematic review and meta-analysis of randomized controlled trials. Seko LM, Moroni RM, Leitao VM, et al. Fertil. Steril. 101(1), 154-161.e4, (2014)

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Partial neural protection with prophylactic low-dose melatonin after asphyxia in preterm fetal sheep. Drury PP, Davidson JO, Bennet L, et al. J. Cereb. Blood Flow Metab. 34(1), 126-35, (2014)

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Melatonin inhibits alcohol-induced increases in duodenal mucosal permeability in rats in vivo. Sommansson A, Saudi WS, Nylander O, et al. Am. J. Physiol. Gastrointest. Liver Physiol. 305(1), G95-G105, (2013)

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Molecular mechanisms of the pro-apoptotic actions of melatonin in cancer: a review. Bizzarri M, Proietti S, Cucina A, et al. Expert Opin. Ther. Targets 17(12), 1483-96, (2013)

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Is melatonin ready to be used in preterm infants as a neuroprotectant? Biran V, Phan Duy A, Decobert F, et al. Dev. Med. Child Neurol. 56(8), 717-23, (2014)

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Melatonin: Quantum-chemical and biochemical investigation of antioxidant activity. Zhivko A Velkov et al Eur. J. Med. Chem. 44, 2834-9, (2009)

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Circadian phase and its relationship to nighttime sleep in toddlers. LeBourgeois MK, Carskadon MA, Akacem LD, et al. J. Biol. Rhythms 28(5), 322-31, (2013)

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Pharmacological interventions for sleepiness and sleep disturbances caused by shift work. Liira J, Verbeek J, and Ruotsalainen J JAMA 313(9), 961-2, (2015)

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Melatonin potentiates cisplatin-induced apoptosis and cell cycle arrest in human lung adenocarcinoma cells. Plaimee P, Weerapreeyakul N, Barusrux S, et al. Cell Prolif. 48(1), 67-77, (2015)

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Longterm melatonin administration alleviates paraquat mediated oxidative stress in Drosophila melanogaster. Medina-Leendertz S, Paz M, Mora M, et al. Invest. Clin. 55(4), 352-64, (2014)

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A reply. Andersen LP Anaesthesia 70(1), 114-5, (2015)

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Melatonin and postoperative pain: can the heterogeneous be pooled? Kuriyama A, Urushidani S, and Sato M Anaesthesia 70(1), 113-4, (2015)

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Melatonin regulating the expression of miRNAs involved in hair follicle cycle of cashmere goats skin. Fu S, Zhao H, Zheng Z, et al. Yi Chuan 36(12), 1235-42, (2014)

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Melatonin modifies cellular stress in the liver of septic mice by reducing reactive oxygen species and increasing the unfolded protein response. Kleber A, Kubulus D, Rössler D, et al. Exp. Mol. Pathol. 97(3), 565-71, (2014)

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Artificial light at night: a neglected population health concern of the built environment. Grose M Health Promot. J. Austr. 25(3), 193-5, (2014)

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Melatonin induces apoptosis through biomolecular changes, in SK-LU-1 human lung adenocarcinoma cells. Plaimee P, Weerapreeyakul N, Thumanu K, et al. Cell Prolif. 47(6), 564-77, (2014)

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Melatonin receptors trigger cAMP production and inhibit chloride movements in nonpigmented ciliary epithelial cells. Huete-Toral F, Crooke A, Martínez-Águila A, et al. J. Pharmacol. Exp. Ther. 352(1), 119-28, (2015)

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Melatonin ameliorates dexamethasone-induced inhibitory effects on the proliferation of cultured progenitor cells obtained from adult rat hippocampus. Ekthuwapranee K, Sotthibundhu A, Tocharus C, et al. J. Steroid Biochem. Mol. Biol. 145, 38-48, (2015)

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Effects of antioxidant agents against cyclosporine-induced hepatotoxicity. Akbulut S, Elbe H, Eris C, et al. J. Surg. Res. 193(2), 658-66, (2015)

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Melatonin potentiates the anti-tumour effect of pravastatin in rat mammary gland carcinoma model. Orendáš P, Kubatka P, Bojková B, et al. Int. J. Exp. Pathol. 95(6), 401-10, (2014)

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Getting rhythm: how do babies do it? Joseph D, Chong NW, Shanks ME, et al. Arch. Dis. Child Fetal Neonatal Ed. 100(1), F50-4, (2015)

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Pharmacological interventions for sleepiness and sleep disturbances caused by shift work. Liira J, Verbeek JH, Costa G, et al. Cochrane Database Syst. Rev. 8, CD009776, (2014)

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Melatonin inhibits thermal injury-induced hyperpermeability in microvascular endothelial cells. Wiggins-Dohlvik K, Han MS, Stagg HW, et al. J. Trauma Acute Care Surg. 77(6), 899-905; discussion 905, (2014)

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[The effect of melatonin on bone tissue metabolism]. Litovka IH, Mazepa-Kryzhanivs'ka YO, and Berezovskyĭ VIa Fiziol. Zh. 60(2), 102-9, (2014)

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What can you tell me about melatonin? Duke. Med. Health. News. 19(9), 8, (2013)

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[The activity of glutathione antioxidant system at melaksen and valdoxan action under experimental hyperthyroidism in rats]. Gorbenko MV, Popova TN, Shul'gin KK, et al. Biomed. Khim. 59(5), 541-9, (2013)

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[Anti-inflammatory potential of melatonin]. Arushanian ÉB and Naumov SS Klin. Med. (Mosk.) 91(7), 18-22, (2013)

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[Melatonin as a drug: present-day status and prospects]. Arushanian ÉB Eksp. Klin. Farmakol. 76(9), 32-7, (2013)

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Twisting the night away: a review of the neurobiology, genetics, diagnosis, and treatment of shift work disorder. Morrissette DA CNS Spectr. 18 Suppl 1, 45-53; quiz 54, (2013)

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[Treatment with ramelteon for sleep disturbance in severely disabled children and young adults]. Miyamoto A, Fukuda I, Tanaka H, et al. No To Hattatsu. 45(6), 440-4, (2013)

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[Melatonin secretion is associated with diabetes risk]. Kreutzkamp B Med. Monatsschr. Pharm. 36(9), 358-9, (2013)

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[Effect of melatonin on the thrombocyte hemostasis and its circadian organization]. Arushanian ÉB Eksp. Klin. Farmakol. 76(5), 32-6, (2013)

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Age-related decline in melatonin and its MT1 receptor are associated with decreased sensitivity to melatonin and enhanced mammary tumor growth. Hill SM, Cheng C, Yuan L, et al. Curr. Aging Sci. 6(1), 125-33, (2013)

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[The use of melatonin in combined therapy of drug-induced hepatitis]. Popov SS, Pashkov AN, Zoloedov VI, et al. Klin. Med. (Mosk.) 91(3), 50-3, (2013)

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[Pineal hormone melatonin in low doses potentiates psychotropic and chronotropic activity of tofisopam in rats]. Abrushanian ÉB and Popov AV Eksp. Klin. Farmakol. 76(4), 15-7, (2013)

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[Universal therapeutic properties of melatonin]. Arushanian ÉB Klin. Med. (Mosk.) 91(2), 4-8, (2013)

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[Protective action of melatonin in experimental glaucoma in rats]. Mykheĭtseva IM Fiziol. Zh. 59(1), 78-83, (2013)

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[Disturbed sleep in children with ADHD: is there a place for melatonin as a treatment option?]. Holvoet E and Gabriëls L Tijdschr. Psychiatr. 55(5), 349-57, (2013)

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[Effects of melatonin on oxygen-dependent processes]. Zinchuk VV, Glutkin SV, Shul'ga EV, et al. Eksp. Klin. Farmakol. 76(2), 32-6, (2013)

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Relaxation drinks: an anti-frazzle fizzle? Consum. Rep. 78(5), 8-9, (2013)

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Daily regulation of hormone profiles. Kalsbeek A and Fliers E Handbook of Experimental Pharmacology (217), 185-226, (2013)

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The circadian control of sleep. Fisher SP, Foster RG, and Peirson SN Handbook of Experimental Pharmacology (217), 157-83, (2013)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Alterations in diurnal rhythmicity in patients treated for nonfunctioning pituitary macroadenoma: a controlled study and literature review. Joustra SD, Thijs RD, van den Berg R, et al. Eur. J. Endocrinol. 171(2), 217-28, (2014)

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Synthesis, inhibitory activity of cholinesterases, and neuroprotective profile of novel 1,8-naphthyridine derivatives. Cristóbal de Los Ríos et al J. Med. Chem. 53, 5129-43, (2010)

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Melatonin and the theories of aging: a critical appraisal of melatonin's role in antiaging mechanisms. Hardeland R J. Pineal Res. 55(4), 325-56, (2013)

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Extrapineal melatonin: sources, regulation, and potential functions. Acuña-Castroviejo D, Escames G, Venegas C, et al. Cell. Mol. Life Sci. 71(16), 2997-3025, (2014)

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Effect of melatonin and cholesterol on the structure of DOPC and DPPC membranes. Drolle E, Kučerka N, Hoopes MI, et al. Biochim. Biophys. Acta 1828(9), 2247-54, (2013)

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Novel tacrine-melatonin hybrids as dual-acting drugs for Alzheimer disease, with improved acetylcholinesterase inhibitory and antioxidant properties. María Isabel Rodríguez-Franco et al J. Med. Chem. 49, 459-62, (2006)

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1,6-Dihydro-2H-indeno[5,4-b]furan derivatives: design, synthesis, and pharmacological characterization of a novel class of highly potent MT?-selective agonists. Tatsuki Koike et al J. Med. Chem. 54, 3436-44, (2011)

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Advances in the research of melatonin in autism spectrum disorders: literature review and new perspectives. Tordjman S, Najjar I, Bellissant E, et al. Int. J. Mol. Sci. 14(10), 20508-42, (2013)

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Melatonin reduces endoplasmic reticulum stress and preserves sirtuin 1 expression in neuronal cells of newborn rats after hypoxia-ischemia. Carloni S, Albertini MC, Galluzzi L, et al. J. Pineal Res. 57(2), 192-9, (2014)

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Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities. Arup Maiti et al J. Med. Chem. 52, 1873-84, (2009)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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N-acylaminophenothiazines: neuroprotective agents displaying multifunctional activities for a potential treatment of Alzheimer's disease. Gema C González-Muñoz et al Eur. J. Med. Chem. 46, 2224-35, (2011)

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Synthesis of a novel series of tricyclic dihydrofuran derivatives: discovery of 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridines as melatonin receptor (MT1/MT2) ligands. Tatsuki Koike et al J. Med. Chem. 54, 4207-18, (2011)

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Small molecule inhibitors of aggregation indicate that amyloid beta oligomerization and fibrillization pathways are independent and distinct. Mihaela Necula et al J. Biol. Chem. 282, 10311-24, (2007)

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Melatonin acts through MT1/MT2 receptors to activate hypothalamic Akt and suppress hepatic gluconeogenesis in rats. Faria JA, Kinote A, Ignacio-Souza LM, et al. Am. J. Physiol. Endocrinol. Metab. 305(2), E230-42, (2013)

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Analysis of structure-activity relationships for MT2 selective antagonists by melatonin MT1 and MT2 receptor models. Silvia Rivara et al J. Med. Chem. 48, 4049-60, (2005)

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Circadian rhythm disorders among adolescents: assessment and treatment options. Bartlett DJ, Biggs SN, and Armstrong SM Med. J. Aust. 199(8), S16-20, (2013)

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cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain responses against carrageenan-induced hyperalgesia. Huaqing Liu et al J. Med. Chem. 51, 7094-8, (2008)

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The relationship between obesity and exposure to light at night: cross-sectional analyses of over 100,000 women in the Breakthrough Generations Study. McFadden E, Jones ME, Schoemaker MJ, et al. Am. J. Epidemiol. 180(3), 245-50, (2014)

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Melatonin as a proteasome inhibitor. Is there any clinical evidence? Vriend J and Reiter RJ Life Sci. 115(1-2), 8-14, (2014)

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7-Substituted-melatonin and 7-substituted-1-methylmelatonin analogues: effect of substituents on potency and binding affinity. Rüdiger Faust et al Bioorg. Med. Chem. 15, 4543-51, (2007)

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A randomized controlled trial with bright light and melatonin for the treatment of delayed sleep phase disorder: effects on subjective and objective sleepiness and cognitive function. Wilhelmsen-Langeland A, Saxvig IW, Pallesen S, et al. J. Biol. Rhythms 28(5), 306-21, (2013)

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Inhibition of VEGF expression through blockade of Hif1α and STAT3 signalling mediates the anti-angiogenic effect of melatonin in HepG2 liver cancer cells. Carbajo-Pescador S, Ordoñez R, Benet M, et al. Br. J. Cancer 109(1), 83-91, (2013)

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Circadian melatonin rhythm and excessive daytime sleepiness in Parkinson disease. Videnovic A, Noble C, Reid KJ, et al. JAMA Neurol. 71(4), 463-9, (2014)

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Mapping the melatonin receptor. 7. Subtype selective ligands based on beta-substituted N-acyl-5-methoxytryptamines and beta-substituted N-acyl-5-methoxy-1-methyltryptamines. Andrew Tsotinis et al J. Med. Chem. 49, 3509-19, (2006)

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The end of a myth: cloning and characterization of the ovine melatonin MT(2) receptor. Cogé F Br. J. Pharmacol. 158(5), 1248-62, (2009)

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Melatonin-induced methylation of the ABCG2/BCRP promoter as a novel mechanism to overcome multidrug resistance in brain tumour stem cells. Martín V, Sanchez-Sanchez AM, Herrera F, et al. Br. J. Cancer 108(10), 2005-12, (2013)

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Association of nocturnal melatonin secretion with insulin resistance in nondiabetic young women. McMullan CJ, Curhan GC, Schernhammer ES, et al. Am. J. Epidemiol. 178(2), 231-8, (2013)

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Toward the definition of stereochemical requirements for MT2-selective antagonists and partial agonists by studying 4-phenyl-2-propionamidotetralin derivatives. Annalida Bedini et al J. Med. Chem. 54, 8362-72, (2011)

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Design and synthesis of 2-phenylimidazo[1,2-a]pyridines as a novel class of melatonin receptor ligands. Saïd El Kazzouli et al Eur. J. Med. Chem. 46, 4252-7, (2011)

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Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity. Cheryl A Grice et al J. Med. Chem. 51, 4150-69, (2008)

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Benzenediol-berberine hybrids: Multifunctional agents for Alzheimer's disease. Huailei Jiang et al Bioorg. Med. Chem. 19, 7228-35, (2011)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Circadian dynamics of the cone-rod homeobox (CRX) transcription factor in the rat pineal gland and its role in regulation of arylalkylamine N-acetyltransferase (AANAT). Rohde K, Rovsing L, Ho AK, et al. Endocrinology 155(8), 2966-75, (2014)

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Melatonin inhibits aromatase promoter expression by regulating cyclooxygenases expression and activity in breast cancer cells. C Martínez-Campa et al Br. J. Cancer 101, 1613-9, (2009)

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2-[(2,3-dihydro-1H-indol-1-yl)methyl]melatonin analogues: a novel class of MT2-selective melatonin receptor antagonists. Zlotos, D., P.; et al. J. Med. Chem. 52, 826, (2009)

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Melatonin receptors mediate improvements of survival in a model of polymicrobial sepsis. Fink T, Glas M, Wolf A, et al. Crit. Care Med. 42(1), e22-31, (2014)

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Design and synthesis of N-(3,3-diphenylpropenyl)alkanamides as a novel class of high-affinity MT2-selective melatonin receptor ligands. Annalida Bedini et al J. Med. Chem. 49, 7393-403, (2006)

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The flavonoid myricetin reduces nocturnal melatonin levels in the blood through the inhibition of serotonin N-acetyltransferase. Shin JC, Jung HY, Harikishore A, et al. Biochem. Biophys. Res. Commun. 440(2), 312-6, (2013)

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Synthesis and characterization of novel indole derivatives reveal improved therapeutic agents for treatment of ischemia/reperfusion (I/R) injury. Bi, W.; et al. J. Med. Chem. 53, 6763, (2010)

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Preparation and pharmacological evaluation of a novel series of 2-(phenylthio)benzo[b]thiophenes as selective MT2 receptor ligands. Christophe Mésangeau et al Eur. J. Med. Chem. 46, 1835-40, (2011)

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Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Alessia Carocci et al Bioorg. Med. Chem. 18, 6496-511, (2010)

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Melatonin renders neuroprotection by protein kinase C mediated aquaporin-4 inhibition in animal model of focal cerebral ischemia. Bhattacharya P, Pandey AK, Paul S, et al. Life Sci. 100(2), 97-109, (2014)

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Therapeutic response of untreatable hepatocellular carcinoma after application of the immune modulators IL-2, BCG and melatonin. Tomov B, Popov D, Tomova R, et al. Anticancer Res. 33(10), 4531-5, (2013)

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Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands. Yueqing Hu et al Bioorg. Med. Chem. Lett. 20, 2582-5, (2010)

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Melatonin influences on steroidogenic gene expression in the ovary of pinealectomized rats. Maganhin CC, Simões RS, Fuchs LF, et al. Fertil. Steril. 102(1), 291-8, (2014)

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Mobile phone radiation induces mode-dependent DNA damage in a mouse spermatocyte-derived cell line: a protective role of melatonin. Liu C, Gao P, Xu SC, et al. Int. J. Radiat. Biol. 89(11), 993-1001, (2013)

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Synthesis, structure, theoretical and experimental in vitro antioxidant/pharmacological properties of ?-aryl, N-alkyl nitrones, as potential agents for the treatment of cerebral ischemia. Abdelouahid Samadi et al Bioorg. Med. Chem. 19, 951-60, (2011)

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Protective effect of melatonin against transient global cerebral ischemia-induced neuronal cell damage via inhibition of matrix metalloproteinase-9. Kim SJ and Lee SR Life Sci. 94(1), 8-16, (2014)

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Effects of melatonin on nervous system aging: neurogenesis and neurodegeneration. Sarlak G, Jenwitheesuk A, Chetsawang B, et al. J. Pharmacol. Sci. 123(1), 9-24, (2013)

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Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT(1) melatoninergic ligands. Christophe Mésangeau et al Bioorg. Med. Chem. 18, 3426-36, (2010)

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Design and synthesis of benzofuranic derivatives as new ligands at the melatonin-binding site MT3. Mohamed Ettaoussi et al Bioorg. Med. Chem. 16, 4954-62, (2008)

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Bivalent ligand approach on N-{2-[(3-methoxyphenyl)methylamino]ethyl}acetamide: synthesis, binding affinity and intrinsic activity for MT(1) and MT(2) melatonin receptors. Gilberto Spadoni et al Bioorg. Med. Chem. 19, 4910-6, (2011)

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Evaluation of the anti-inflammatory and anti-nociceptive activities of novel synthesized melatonin analogues. Gamal A Elmegeed et al Eur. J. Med. Chem. 42, 1285-92, (2007)

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Immunomodulatory effect of melatonin in SK-LU-1 human lung adenocarcinoma cells co-cultured with peripheral blood mononuclear cells. Plaimee P, Khamphio M, Weerapreeyakul N, et al. Cell Prolif. 47(5), 406-15, (2014)

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Design, synthesis, and melatoninergic activity of new azido- and isothiocyanato-substituted indoles. Tsotinis, A.; et al. J. Med. Chem. 50, 6436, (2007)

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Design and synthesis of naphthalenic derivatives as new ligands at the melatonin binding site MT3. Véronique Leclerc et al Eur. J. Med. Chem. 46, 1622-9, (2011)

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Synthesis and biological activity of new melatonin dimeric derivatives. Barbara Di Giacomo et al Bioorg. Med. Chem. 15, 4643-50, (2007)

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Melatonin reduces ulcerative colitis-associated local and systemic damage in mice: investigation on possible mechanisms. Trivedi PP and Jena GB Dig. Dis. Sci. 58(12), 3460-74, (2013)

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Disassembly of preformed amyloid beta fibrils by small organofluorine molecules. Abha Sood et al Bioorg. Med. Chem. Lett. 21, 2044-7, (2011)

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Design and synthesis of 3-phenyltetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands. Part II. Sophie Durieux et al Bioorg. Med. Chem. 17, 2963-74, (2009)

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Melatonin attenuates the skin sympathetic nerve response to mental stress. Muller MD, Sauder CL, and Ray CA Am. J. Physiol. Heart Circ. Physiol. 305(9), H1382-6, (2013)

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Oxidative damage of rat liver mitochondria during exposure to t-butyl hydroperoxide. Role of Ca²⁺ ions in oxidative processes. Zavodnik IB, Dremza IK, Cheshchevik VT, et al. Life Sci. 92(23), 1110-7, (2013)

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Synthesis of 3-phenylnaphthalenic derivatives as new selective MT(2) melatoninergic ligands. Sophie Poissonnier-Durieux et al Bioorg. Med. Chem. 16, 8339-48, (2008)

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A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta. Ashley A Reinke et al Bioorg. Med. Chem. Lett. 19, 4952-7, (2009)

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Melatonin improves humoral and cell-mediated immune responses of male golden hamster following stress induced by dexamethasone. Vishwas DK, Mukherjee A, and Haldar C J. Neuroimmunol. 259(1-2), 17-25, (2013)

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Clocks for all seasons: unwinding the roles and mechanisms of circadian and interval timers in the hypothalamus and pituitary. Wood S and Loudon A J. Endocrinol. 222(2), R39-59, (2014)

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Update on the role of melatonin in the prevention of cancer tumorigenesis and in the management of cancer correlates, such as sleep-wake and mood disturbances: review and remarks. Rondanelli M, Faliva MA, Perna S, et al. Aging Clin. Exp. Res. 25(5), 499-510, (2013)

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Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands. Mohamed I Attia et al Bioorg. Med. Chem. 16, 7654-61, (2008)

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Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands. Christian Markl et al Bioorg. Med. Chem. 17, 4583-94, (2009)

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Potent neuroprotective role of novel melatonin derivatives for management of central neuropathy induced by acrylamide in rats. Hanaa H Ahmed et al Eur. J. Med. Chem. 45, 5452-9, (2010)

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A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site. Hongying Du et al Eur. J. Med. Chem. 43, 2861-9, (2008)

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Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists. Matthieu Jeanty et al Bioorg. Med. Chem. Lett. 21, 2316-9, (2011)

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Melatonin and its analog 5-methoxycarbonylamino-N-acetyltryptamine potentiate adrenergic receptor-mediated ocular hypotensive effects in rabbits: significance for combination therapy in glaucoma. Crooke A, Huete-Toral F, Martínez-Águila A, et al. J. Pharmacol. Exp. Ther. 346(1), 138-45, (2013)

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Melatonin receptor type 1 signals to extracellular signal-regulated kinase 1 and 2 via Gi and Gs dually coupled pathways in HEK-293 cells. Chen L, He X, Zhang Y, et al. Biochemistry 53(17), 2827-39, (2014)

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Antioxidant activity of benzoxazolinonic and benzothiazolinonic derivatives in the LDL oxidation model. Ismaël Yekini et al Bioorg. Med. Chem. 17, 7823-30, (2009)

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A molecular and chemical perspective in defining melatonin receptor subtype selectivity. Chan KH and Wong YH Int. J. Mol. Sci. 14(9), 18385-406, (2013)

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Phenylpyrrole derivatives as neural and inducible nitric oxide synthase (nNOS and iNOS) inhibitors. Luisa C López Cara et al Eur. J. Med. Chem. 44, 2655-66, (2009)

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Design and synthesis of 4-arylpiperidinyl amide and N-arylpiperdin-3-yl-cyclopropane carboxamide derivatives as novel melatonin receptor ligands. Guiying Li et al Bioorg. Med. Chem. Lett. 21, 1236-42, (2011)

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Melatonin and dopamine as biomarkers to optimize treatment in phenylketonuria: effects of tryptophan and tyrosine supplementation. Yano S, Moseley K, and Azen C J. Pediatr. 165(1), 184-189.e1, (2014)

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The relationship between bipolar disorder and biological rhythms. Gonzalez R J. Clin. Psychiatry 75(4), e323-31, (2014)

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Synthesis and in vivo anti-mutagenic activity of novel melatonin derivatives. Gamal A Elmegeed et al Eur. J. Med. Chem. 43, 763-70, (2008)

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Design, synthesis and melatoninergic activity of new unsubstituted and beta,beta'-difunctionalised 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-6-alkanamides. Andrew Tsotinis et al Eur. J. Med. Chem. 42, 1004-13, (2007)

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Norepinephrine activates NF-κB transcription factor in cultured rat pineal gland. Villela D, de Sá Lima L, Peres R, et al. Life Sci. 94(2), 122-9, (2014)

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(2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-8-yl)-acetic acid: An aldose reductase inhibitor and antioxidant of zwitterionic nature. Milan Stefek et al Bioorg. Med. Chem. 19, 7181-5, (2011)

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Anti-fibrotic and anti-inflammatory properties of melatonin on human gingival fibroblasts in vitro. Gómez-Florit M, Ramis JM, and Monjo M Biochem. Pharmacol. 86(12), 1784-90, (2013)

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(R)-2-(4-Phenylbutyl)dihydrobenzofuran derivatives as melatoninergic agents. Li-Qiang Sun et al Bioorg. Med. Chem. Lett. 15, 1345-9, (2005)

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Short-duration judgment in young Indian subjects under 30 h constant wakefulness. Pande B, Parganiha A, Patra PK, et al. Indian J. Exp. Biol. 52(5), 559-68, (2014)

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Daily variation in melatonin level, antioxidant activity and general immune response of peripheral blood mononuclear cells and lymphoid tissues of Indian goat Capra hircus during summer and winter. Singh AK, Ghosh S, Basu P, et al. Indian J. Exp. Biol. 52(5), 467-77, (2014)

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[Involvement of melatonin MT2 receptor mutants in type 2 diabetes development]. Karamitri A, Vincens M, Chen M, et al. Med. Sci. (Paris.) 29(8-9), 778-84, (2013)

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The pineal regulation of the immune system: 40 years since the discovery. Csaba G Acta Microbiol. Immunol. Hung. 60(2), 77-91, (2013)

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NADPH oxidase inhibitor, apocynin, improves renal glutathione status in Zucker diabetic fatty rats: a comparison with melatonin. Winiarska K, Focht D, Sierakowski B, et al. Chem. Biol. Interact. 218, 12-9, (2014)

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Effect of the combination of metformin hydrochloride and melatonin on oxidative stress before and during pregnancy, and biochemical and histopathological analysis of the livers of rats after treatment for polycystic ovary syndrome. Lemos AJ, Peixoto CA, Teixeira AA, et al. Toxicol. Appl. Pharmacol. 280(1), 159-68, (2014)

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A combined effect of dextromethorphan and melatonin on neuropathic pain behavior in rats. Shuxing Wang et al Brain Res. 1288, 42-9, (2009)

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N-nitrosomelatonin enhances photic synchronization of mammalian circadian rhythms. Baidanoff FM, Plano SA, Doctorovich F, et al. J. Neurochem. 129(1), 60-71, (2014)

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Role of progesterone in melatonin-mediated protection against acute kidney injury. Sehajpal J, Kaur T, Bhatti R, et al. J. Surg. Res. 191(2), 441-7, (2014)

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Toxicity induced by chemical warfare agents: insights on the protective role of melatonin. Pita R, Marco-Contelles J, Ramos E, et al. Chem. Biol. Interact. 206(2), 134-42, (2013)

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Melatonin: its possible role in the management of viral infections--a brief review. Silvestri M and Rossi GA Ital. J. Pediatr. 39, 61, (2013)

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Blood pressure reducing effects of piromelatine and melatonin in spontaneously hypertensive rats. Huang L, Zhang C, Hou Y, et al. Eur. Rev. Med. Pharmacol. Sci. 17(18), 2449-56, (2013)

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Effectiveness of melatonin for sleep impairment post paediatric acquired brain injury: evidence from a systematic review. Keegan LJ, Reed-Berendt R, Neilly E, et al. Dev. Neurorehabil. 17(5), 355-62, (2014)

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Melatonin effect on the ultrastructure of Ehrlich ascites tumor cells, lifetime and histopathology in Swiss mice. Batista AP, da Silva TG, Teixeira ÁA, et al. Life Sci. 93(23), 882-8, (2013)

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Protective role of melatonin in neonatal diseases. Gitto E, Marseglia L, Manti S, et al. Oxid. Med. Cell. Longev. 2013, 980374, (2013)

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Melatonin, But not auxin, affects postnatal reproductive development in the marsh rice rat (Oryzomys palustris). Edmonds KE Zoolog. Sci. 30(6), 439-45, (2013)

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Effects of melatonin on superovulation and transgenic embryo transplantation in small-tailed han sheep (Ovis aries). Zhang L, Chai M, Tian X, et al. Neuro Endocrinol. Lett. 34(4), 294-301, (2013)

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Modulation of pineal activity during the 23rd sunspot cycle: melatonin rise during the ascending phase of the cycle is accompanied by an increase of the sympathetic tone. Bartsch C, Bartsch H, Seebald E, et al. Indian J. Exp. Biol. 52(5), 438-47, (2014)

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Melatonin: an internal signal for daily and seasonal timing. Trivedi AK and Kumar V Indian J. Exp. Biol. 52(5), 425-37, (2014)

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Assessment of the relationship between melatonin, hormones of the pituitary-ovarian, -thyroid and -adrenocortical axes, and osteoprotegerin and its ligand sRANKL in girls with anorexia nervosa. Ostrowska Z, Ziora K, Oświęcimska J, et al. Postepy Hig. Med. Dosw. (Online) 67, 433-41, (2013)

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Serotoninergic and melatoninergic systems are expressed in mouse embryonic fibroblasts NIH3T3 cells. Liu YJ, Meng FT, Wu L, et al. Neuro Endocrinol. Lett. 34(3), 236-40, (2013)

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[Night shift work and prolactin as a breast cancer risk factor]. Bukowska A and Pepłońska B Med. Pr. 64(2), 245-57, (2013)

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[Experimental and clinical evidence for anticonvulsant activity of melatonin]. Arushanian EB Zh. Nevrol. Psikhiatr. Im. S. S. Korsakova 113(11), 111-5, (2013)

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Re: Persistence of 1,25D-induced hypercalciuria in alendronate treated genetic hypercalciuric stone-forming rats fed a low calcium diet. Assimos DG J. Urol. 192(2), 615, (2014)

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Perioperative melatonin: not ready for prime time. Andersen LP, Rosenberg J, and Gögenur I Br. J. Anaesth. 112(1), 7-8, (2014)

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Melatonin level and risk for type 2 diabetes--in reply. McMullan CJ, Schernhammer ES, and Forman JP JAMA 310(5), 537, (2013)

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Melatonin level and risk for type 2 diabetes. Abbott SM and Zee PC JAMA 310(5), 536-7, (2013)

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Melatonin for sundown syndrome and delirium in dementia: is it effective? Lammers M and Ahmed AI J. Am. Geriatr. Soc. 61(6), 1045-6, (2013)

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Perspective: casting light on sleep deficiency. Czeisler CA Nature 497(7450), S13, (2013)

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Chronobiology: stepping out of time. Eisenstein M Nature 497(7450), S10-2, (2013)

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Melatonin: comprehensive profile. Al-Omary FA Profiles Drug Subst. Excip. Relat. Methodol. 38, 159-226, (2013)

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Merck 14,5816

Beil. 22,V,12,42

FT-IR 2 (3), 3606:D / FT-IR 1 (2), 677:A / FT-NMR 1 (3), 156:C / IR-Spectra (3), 1260:A / IR-Spectra (2), 1095:G / NMR-Reference 2 (2), 546:C / RegBook 1 (2), 2421:A / Sigma FT-IR 1 (1), 678:D / Structure Index 1, 384:D:3

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