Home Amines 1210-83-9
1210-83-9,MFCD00005656
Catalog No.:AA003SLT

1210-83-9 | N-Acetyl-5-hydroxytryptamine

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003SLT
Chemical Name:
N-Acetyl-5-hydroxytryptamine
CAS Number:
1210-83-9
Molecular Formula:
C12H14N2O2
Molecular Weight:
218.2518
MDL Number:
MFCD00005656
SMILES:
CC(=O)NCCc1c[nH]c2c1cc(O)cc2
Properties
Properties
 
BP:
556.8°C at 760 mmHg  
Form:
Solid  
MP:
120-122 °C(lit.)  
Solubility:
ethanol: 50 mg/mL  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
257  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
0.5  

Downstream Synthesis Route

[1]Somei,Masanori;Fukui,Yoshikazu[Heterocycles,1993,vol.36,#8,p.1859-1866]

[1]Glennon,RichardA.;Hong,Seoung-Soo;Bondarev,Mikhail;Law,Ho;Dukat,Malgorzata;Rakhit,Suman;Power,Patricia;Fan,Ermei;Kinneau,Diana;Kamboj,Rajender;Teitler,Milt;Herrick-Davis,Katharine;Smith,Carol[JournalofMedicinalChemistry,1996,vol.39,#1,p.314-322]

[2]Locationinpatent:experimentalpartMarkl,Christian;Clafshenkel,WilliamP.;Attia,MohamedI.;Sethi,Shalini;Witt-Enderby,PaulaA.;Zlotos,DariusP.[ArchivderPharmazie,2011,vol.344,#10,p.666-674]

[3]Glennon;Hong;Dukat;Teitler;Davis[JournalofMedicinalChemistry,1994,vol.37,#18,p.2828-2830]

[4]CurrentPatentAssignee:ARTEREZ-WO2021/62298,2021,A1Locationinpatent:Paragraph0284;0285

[5]Winand,Lea;Schneider,Pascal;Kruth,Sebastian;Greven,Nico-Joel;Hiller,Wolf;Kaiser,Marcel;Pietruszka,Jörg;Nett,Markus[OrganicLetters,2021,vol.23,#16,p.6563-6567]

[6]Schneider,Pascal;Henßen,Birgit;Paschold,Beatrix;Chapple,BenjaminP.;Schatton,Marcel;Seebeck,FlorianP.;Classen,Thomas;Pietruszka,Jörg[AngewandteChemie-InternationalEdition,2021,vol.60,#43,p.23412-23418][Angew.Chem.,2021,vol.133,#43,p.23600-23606]

[1]Glennon;Hong;Dukat;Teitler;Davis[JournalofMedicinalChemistry,1994,vol.37,#18,p.2828-2830]

[1]Somei,Masanori;Fukui,Yoshikazu;Hasegawa,Masakazu[Heterocycles,1995,vol.41,#10,p.2157-2160]

[2]Horstman,JosephA.;Wrona,MonikaZ.;Dryhurst,Glenn[BioorganicChemistry,2002,vol.30,#5,p.371-382]

693-67-4    1210-83-9   
N-2-(5-Undecyloxy-1H-indol-3-yl)-ethyl-acetamide 

[1]Glennon,RichardA.;Hong,Seoung-Soo;Bondarev,Mikhail;Law,Ho;Dukat,Malgorzata;Rakhit,Suman;Power,Patricia;Fan,Ermei;Kinneau,Diana;Kamboj,Rajender;Teitler,Milt;Herrick-Davis,Katharine;Smith,Carol[JournalofMedicinalChemistry,1996,vol.39,#1,p.314-322]

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Journal: Indian journal of experimental biology 20100801

Title: Adrenoceptor expression and diurnal rhythms of melatonin and its precursors in the pineal gland of type 2 diabetic goto-kakizaki rats.

Journal: Endocrinology 20100601

Title: The role of cyanopterin in UV/blue light signal transduction of cyanobacterium Synechocystis sp. PCC 6803 phototaxis.

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Title: Cloning and characterization of a Chlamydomonas reinhardtii cDNA arylalkylamine N-acetyltransferase and its use in the genetic engineering of melatonin content in the Micro-Tom tomato.

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Title: Products of tryptophan catabolism induce Ca2+ release and modulate the cell cycle of Plasmodium falciparum malaria parasites.

Journal: Journal of pineal research 20051001

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Journal: Journal of biological rhythms 20051001

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Journal: Analytical chemistry 20050815

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Journal: Journal of pineal research 20050801

Title: Antioxidant effects of N-acetylserotonin: possible mechanisms and clinical implications.

Journal: Annals of the New York Academy of Sciences 20050801

Title: Immune-modulating effects of melatonin, N-acetylserotonin, and N-acetyldopamine.

Journal: Annals of the New York Academy of Sciences 20050801

Title: N-acetyldopamine inhibits rat brain lipid peroxidation induced by lipopolysaccharide.

Journal: Annals of the New York Academy of Sciences 20050801

Title: Corticosterone modulates noradrenaline-induced melatonin synthesis through inhibition of nuclear factor kappa B.

Journal: Journal of pineal research 20050401

Title: Protective effects of N-acetylserotonin against 6-hydroxydopamine-induced neurotoxicity.

Journal: Life sciences 20050325

Title: Failure to respond to endogenous or exogenous melatonin may cause nonphotoresponsiveness in Harlan Sprague Dawley rats.

Journal: Journal of circadian rhythms 20050101

Title: Retinal ganglion cells are autonomous circadian oscillators synthesizing N-acetylserotonin during the day.

Journal: The Journal of biological chemistry 20041203

Title: The circadian rhythm of 5-HT biosynthetic and degradative enzymes in immortalized mouse neuroendocrine pineal cell line--a model for studying circadian rhythm.

Journal: Life sciences 20041105

Title: Protective effect of N-acetyl-serotonin on the nonenzymatic lipid peroxidation in rat testicular microsomes and mitochondria.

Journal: Journal of pineal research 20041001

Title: Diurnal rhythms in cocaine sensitization and in Period1 levels are common across rodent species.

Journal: Pharmacology, biochemistry, and behavior 20040901

Title: Evaluation of 5-hydroxytryptophol and other endogenous serotonin (5-hydroxytryptamine) analogs as substrates for UDP-glucuronosyltransferase 1A6.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20040801

Title: Involvement of the pineal gland in diurnal cocaine reward in mice.

Journal: European journal of pharmacology 20040412

Title: Serotonin metabolism in rat skin: characterization by liquid chromatography-mass spectrometry.

Journal: Archives of biochemistry and biophysics 20040101

Title: Peroxynitrite scavenging activity of indole derivatives: interaction of indoles with peroxynitrite.

Journal: Journal of medicinal food 20040101

Title: Expression of human organic anion transporters in the choroid plexus and their interactions with neurotransmitter metabolites.

Journal: Journal of pharmacological sciences 20031201

Title: Protective effect of indoleamines on in vitro ascorbate-Fe2+ dependent lipid peroxidation of rod outer segment membranes of bovine retina.

Journal: Journal of pineal research 20031101

Title: Melatonin and N-acetyl-serotonin cross the red blood cell membrane and evoke calcium mobilization in malarial parasites.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20031101

Title: Tryptophan hydroxylase expression in human skin cells.

Journal: Biochimica et biophysica acta 20031015

Title: Melatonin attenuates alpha-adrenergic-induced contractions by increasing the release of vasoactive intestinal peptide in isolated rat penile bulb.

Journal: Urological research 20030801

Title: Characterization of the serotoninergic system in the C57BL/6 mouse skin.

Journal: European journal of biochemistry 20030801

Title: Functional activity of serotoninergic and melatoninergic systems expressed in the skin.

Journal: Journal of cellular physiology 20030701

Title: Chemiluminescence determination of melatonin and some of its derivatives using potassium permanganate and formaldehyde system.

Journal: Analytical and bioanalytical chemistry 20030701

Title: Melatonin biological activity and binding sites in human melanoma cells.

Journal: Journal of pineal research 20030501

Title: Differential effects of lipopolysaccharide on lipid peroxidation in F344N, SHR rats and BALB/c mice, and protection of melatonin and NAS against its toxicity.

Journal: Annals of the New York Academy of Sciences 20030501

Title: Mitochondria as a target for neurotoxins and neuroprotective agents.

Journal: Annals of the New York Academy of Sciences 20030501

Title: Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.

Journal: Journal of medicinal chemistry 20030410

Title: Characterization of melatonin high-affinity binding sites in purified cell nuclei of the hamster (Mesocricetus auratus) harderian gland.

Journal: Journal of pineal research 20030401

Title: Effect of antisense oligodeoxynucleotide for sepiapterin reductase on the viability of PC12 cells in the presence of exogenous carbonyl compounds.

Journal: Chemico-biological interactions 20030201

Title: Melatonin and jet lag syndrome: experimental model and clinical implications.

Journal: CNS spectrums 20030201

Title: Wavelength-dependent induction of a mycosporine-like amino acid in a rice-field cyanobacterium, Nostoc commune: role of inhibitors and salt stress.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20030201

Title: The effect of N-acetyl serotonin on ultraviolet-radiation-induced cataracts in rats.

Journal: Ophthalmologica. Journal international d'ophtalmologie. International journal of ophthalmology. Zeitschrift fur Augenheilkunde 20030101

Title: Photochemical properties of kynurenine pathway metabolites and indoleamines.

Journal: Advances in experimental medicine and biology 20030101

Title: Serotonin precursor (5-hydroxytryptophan) has a profound effect on the post-copulatory time-fixed sexually refractory stage in the male cricket, Gryllus bimaculatus DeGeer.

Journal: Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology 20021101

Title: Serotoninergic system in hamster skin.

Journal: The Journal of investigative dermatology 20021001

Title: Melatonin's unique radical scavenging properties - roles of its functional substituents as revealed by a comparison with its structural analogs.

Journal: Journal of pineal research 20020801

Title: Control of melatonin synthesis in the mammalian pineal gland: the critical role of serotonin acetylation.

Journal: Cell and tissue research 20020701

Title: Serotoninergic and melatoninergic systems are fully expressed in human skin.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020601

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Neuronal expression of arylalkylamine N-acetyltransferase (AANAT) mRNA in the rat brain.

Journal: Neuroscience research 20020401

Title: The neuroprotective activities of melatonin against the Alzheimer beta-protein are not mediated by melatonin membrane receptors.

Journal: Journal of pineal research 20020401

Title: Receptor-mediated modulation of avian caecal muscle contraction by melatonin: role of tyrosine protein kinase.

Journal: Journal of pineal research 20020401

Title: 2[125I]Iodomelatonin binding sites in guinea pig platelets.

Journal: Journal of pineal research 20020301

Title: Conversion of L-tryptophan to serotonin and melatonin in human melanoma cells.

Journal: FEBS letters 20020130

Title: Locally synthesized angiotensin modulates pineal melatonin generation.

Journal: Journal of neurochemistry 20020101

Title: Impact of UVA exposure on psychological parameters and circulating serotonin and melatonin.

Journal: BMC dermatology 20020101

Title: The effect of copper on (3H)-tryptophan metabolism in organ cultures of rat pineal glands.

Journal: Metabolic brain disease 20011201

Title: [Morphofunctional changes in the pineal gland during adaptation to hypothermia].

Journal: Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20011201

Title: Melatonin and N-acetylserotonin inhibit leukocyte rolling and adhesion to rat microcirculation.

Journal: European journal of pharmacology 20011102

Title: N-acetylserotonin suppresses hepatic microsomal membrane rigidity associated with lipid peroxidation.

Journal: European journal of pharmacology 20011005

Title: Carboxy-PTIO increases the tetrahydrobiopterin level in mouse brain microvascular endothelial cells.

Journal: Japanese journal of pharmacology 20010901

Title: Antioxidant and antiaging activity of N-acetylserotonin and melatonin in the in vivo models.

Journal: Annals of the New York Academy of Sciences 20010601

Title: Glucocorticoid receptors and serotonin N-acetyltransferase activity in the fish pineal organ.

Journal: Neuroreport 20010417

Title: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin.

Journal: Journal of clinical psychopharmacology 20010401

Title: Prolonged swim-test immobility of serotonin N-acetyltransferase (AANAT)-mutant mice.

Journal: Journal of pineal research 20010401

Title: Mechanistic studies on the alkyltransferase activity of serotonin N-acetyltransferase.

Journal: Chemistry & biology 20010401

Title: Comparison of the protective effect of melatonin with other antioxidants in the hamster kidney model of estradiol-induced DNA damage.

Journal: Mutation research 20010301

Title: Characterisation of P2Y(1)-like receptor in cultured rat pineal glands.

Journal: European journal of pharmacology 20010301

Title: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes.

Journal: European journal of clinical pharmacology 20010301

Title: N-acetyl-serotonin reduces copper (I) ion-induced lipid peroxidation in bovine retinal homogenates.

Journal: Acta ophthalmologica Scandinavica 20010201

Title: Lesions of the dorsomedial hypothalamic nucleus do not influence the daily profile of pineal metabolism in rats.

Journal: Neuroendocrinology 20010201

Title: Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in rats.

Journal: Journal of cellular biochemistry 20010101

Title: Relative efficacies of indole antioxidants in reducing autoxidation and iron-induced lipid peroxidation in hamster testes.

Journal: Journal of cellular biochemistry 20010101

Title: Modulation of blood glucose by melatonin: a direct action on melatonin receptors in mouse hepatocytes.

Journal: Biological signals and receptors 20010101

Title: Jang SW, et al. N-acetylserotonin activates TrkB receptor in a circadian rhythm. Proc Natl Acad Sci U S A. 2010 Feb 23;107(8):3876-81.

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Tags:1210-83-9 Molecular Formula|1210-83-9 MDL|1210-83-9 SMILES|1210-83-9 N-Acetyl-5-hydroxytryptamine |Heterocyclic_Building_Blocks