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A1824 Sigma

N-Acetyl-5-hydroxytryptamine

≥99% (TLC), powder

Synonym: N-Acetylserotonin, Normelatonin

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Properties

Related Categories Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, GPCR Modulators, GPCR Proteins, Modulators and Antibodies,
assay   ≥99% (TLC)
form   powder
color   white
mp   120-122 °C(lit.)
solubility   ethanol: soluble50 mg/mL
storage temp.   2-8°C
Gene Information   human ... MTNR1A(4543), MTNR1B(4544)

Description

Packaging

1 g in poly bottle

100, 250 mg in poly bottle

Biochem/physiol Actions

Immediate precursor of melatonin. It is formed from serotonin and acetyl-CoA in a reaction catalyzed by serotonin N-acetyl transferase, the rate-limiting enzyme in melatonin biosynthesis. This indoleamine is a weak agonist at melatonin receptors, and has moderate effects on G-protein stimulation and inhibition of cAMP accumulation.

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.

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

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Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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Comparison of the pharmacological characteristics of 2-[125I]iodomelatonin binding sites in the lung, spleen, brain and kidney of chicken. Pang, C.S., et al. Biol. Signals 4, 311, (1995)

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Developmental changes and daily rhythm in melatonin-induced inhibition of 3',5'-cyclic AMP accumulation in the rat pituitary. Vanecek, J., and Vollrath, L. Endocrinology 126, 1509-1513, (1990)

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Indoleamine analogs as probes of the substrate selectivity and catalytic mechanism of serotonin N-acetyltransferase. Khalil, E.M., et al. J. Biol. Chem. 273, 30321-30327, (1998)

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Pharmacological characterisation of melatonin mt1 receptor-mediated stimulation of [35S]-GTPγS binding. Beresford, I.J., et al. Biochem. Pharmacol. 56, 1167-1174, (1998)

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Melatonin receptor pharmacology: toward subtype specificity. Sugden, D., et al. Biol. Cell 89, 531-537, (1998)

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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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Metabolism of melatonin and biological activity of intermediates of melatoninergic pathway in human skin cells. Kim TK, Kleszczynski K, Janjetovic Z, et al. FASEB J. 27(7), 2742-55, (2013)

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Enhanced production of melatonin by ectopic overexpression of human serotonin N-acetyltransferase plays a role in cold resistance in transgenic rice seedlings. Kang K, Lee K, Park S, et al. J. Pineal Res. 49(2), 176-82, (2010)

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N-acetylserotonin activates TrkB receptor in a circadian rhythm. Jang SW, Liu X, Pradoldej S, et al. Proc. Natl. Acad. Sci. U. S. A. 107(8), 3876-81, (2010)

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Altered interactions of tryptophan metabolites in first-episode neuroleptic-naive patients with schizophrenia. Yao JK, Dougherty GG, Reddy RD, et al. Mol. Psychiatry 15(9), 938-53, (2010)

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N-acetylserotonin: neuroprotection, neurogenesis, and the sleepy brain. Tosini G, Ye K, and Iuvone PM Neuroscientist 18(6), 645-53, (2012)

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Acute inhibition of guanosine triphosphate cyclohydrolase 1 uncouples endothelial nitric oxide synthase and elevates blood pressure. Wang S, Xu J, Song P, et al. Hypertension 52(3), 484-90, (2008)

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Circadian regulation of pineal gland rhythmicity. Borjigin J, Zhang LS, and Calinescu AA Mol. Cell. Endocrinol. 349(1), 13-9, (2012)

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Metabolism of melatonin by cytochrome P450s in rat liver mitochondria and microsomes. Semak I, Korik E, Antonova M, et al. J. Pineal Res. 45(4), 515-23, (2008)

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Effect of selected antioxidants in beta-cyfluthrin-induced oxidative stress in human erythrocytes in vitro. Sadowska-Woda I, Wójcik N, Karowicz-Bilińska A, et al. Toxicol. In Vitro 24(3), 879-84, (2010)

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N-acetylserotonin promotes hippocampal neuroprogenitor cell proliferation in sleep-deprived mice. Sompol P, Liu X, Baba K, et al. Proc. Natl. Acad. Sci. U. S. A. 108(21), 8844-9, (2011)

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Changes in the content of brain biogenic amine associated with early colony establishment in the Queen of the ant, Formica japonica. Aonuma H and Watanabe T PLoS ONE 7(8), e43377, (2012)

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Tryptophan hydroxylase is modulated by L-type calcium channels in the rat pineal gland. Barbosa R, Scialfa JH, Terra IM, et al. Life Sci. 82(9-10), 529-35, (2008)

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Effect of methylene blue and related redox dyes on monoamine oxidase activity; rat pineal content of N-acetylserotonin, melatonin, and related indoles; and righting reflex in melatonin-primed frogs. Oxenkrug GF, Sablin SO, and Requintina PJ Ann. N. Y. Acad. Sci. 1122, 245-52, (2007)

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The melatonin-producing system is fully functional in retinal pigment epithelium (ARPE-19). Zmijewski MA, Sweatman TW, and Slominski AT Mol. Cell. Endocrinol. 307(1-2), 211-6, (2009)

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Melatonin administration after pilocarpine-induced status epilepticus: a new way to prevent or attenuate postlesion epilepsy? Lima E, Cabral FR, Cavalheiro EA, et al. Epilepsy Behav. 20(4), 607-12, (2011)

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N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells. Yoshimitsu Yamazaki et al Bioorg. Med. Chem. Lett. 19, 4178-82, (2009)

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Pineal arylalkylamine N-acetyltransferase (Aanat) gene expression as a target of inflammatory mediators in the chicken. Piesiewicz A, Kedzierska U, Adamska I, et al. Gen. Comp. Endocrinol. 179(2), 143-51, (2012)

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Quantitation of melatonin and n-acetylserotonin in human plasma by nanoflow LC-MS/MS and electrospray LC-MS/MS. Carter MD, Calcutt MW, Malow BA, et al. J. Mass Spectrom. 47(3), 277-85, (2012)

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The antioxidant behaviour of melatonin and structural analogues during lipid peroxidation depends not only on their functional groups but also on the assay system. Fagali N and Catalá A Biochem. Biophys. Res. Commun. 423(4), 873-7, (2012)

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N-acetylserotonin increases cell proliferation and differentiating neuroblasts with tertiary dendrites through upregulation of brain-derived neurotrophic factor in the mouse dentate gyrus. Yoo DY, Nam SM, Kim W, et al. J. Vet. Med. Sci. 73(11), 1411-6, (2011)

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RGS2 is a feedback inhibitor of melatonin production in the pineal gland. Matsuo M, Coon SL, and Klein DC FEBS Lett. 587(9), 1392-8, (2013)

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Photocatalytic mechanisms of indoleamine destruction by the quinalphos metabolite 2-hydroxyquinoxaline: a study on melatonin and its precursors serotonin and N-acetylserotonin. Behrends A, Riediger S, Grube S, et al. J. Environ. Sci. Health B 42(6), 599-606, (2007)

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Protective effects of melatonin and N-acetylserotonin on aflatoxin B1-induced lipid peroxidation in rats. Gesing A and Karbownik-Lewinska M Cell Biochem. Funct. 26(3), 314-9, (2008)

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In vitro effects of 5-hydroxytryptophan, indoleamines and leptin on arylalkylamine N-acetyltransferase (AA-NAT) activity in pineal organ of the fish, Clarias gariepinus (Burchell, 1822) during different phases of the breeding cycle. Gupta BB, Yanthan L, and Singh KM Indian J. Exp. Biol. 48(8), 786-92, (2010)

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Relative efficacies of alpha-tocopherol, N-acetyl-serotonin, and melatonin in reducing non-enzymatic lipid peroxidation of rat testicular microsomes and mitochondria. Gavazza M and Catalá A Mol. Cell Biochem. 321(1-2), 37-43, (2009)

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N-acetylserotonin reduces lipopolysaccharide-induced lipid peroxidation in vitro more effectively than melatonin. Stuss M, Wiktorska JA, and Sewerynek E Neuro Endocrinol. Lett. 31(4), 489-96, (2010)

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Melatonin formation in pineal gland from rats with hexachlorobenzene experimental porphyria. Llambías EB, Mazzetti MB, Lelli SM, et al. Int. J. Toxicol. 26(6), 545-51, (2007)

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Corp MSDS 1, 41:B / FT-IR 1 (2), 674:D / FT-IR 2 (3), 3599:C / FT-NMR 1 (3), 147:C / IR-Spectra (2), 1093:F / IR-Spectra (3), 1257:H / NMR-Reference 2 (2), 543:A / RegBook 1 (2), 2415:M / Sigma FT-IR 1 (2), 2:C / Structure Index 1, 383:D:5

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