N-ACETYLSEROTONIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H14N2O2
Molecular Weight	218.2518
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NCCC1=CNC2=C1C=C(O)C=C2

InChI

InChIKey=MVAWJSIDNICKHF-UHFFFAOYSA-N

InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Potency
Melatonin receptor type 1B 4 Target ID: P49286 Gene ID: 4544.0 Gene Symbol: MTNR1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10455277	Agonist 2752	6.47 null [pKi]
Neurotrophic tyrosine kinase receptor type 2 14 Target ID: CHEMBL4898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20133677	Agonist 2752
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16179540	Inhibitor 8504

PubMed

Title	Date	PubMed
Central administration of growth hormone-releasing hormone triggers downstream movement and schooling behavior of chum salmon (Oncorhynchus keta) fry in an artificial stream.	2009-03	19068234
Local corticosterone infusion enhances nocturnal pineal melatonin production in vivo.	2009-02	19076264
Relative efficacies of alpha-tocopherol, N-acetyl-serotonin, and melatonin in reducing non-enzymatic lipid peroxidation of rat testicular microsomes and mitochondria.	2009-01	18758914
Metabolism of melatonin by cytochrome P450s in rat liver mitochondria and microsomes.	2008-11	18717775
Acute inhibition of guanosine triphosphate cyclohydrolase 1 uncouples endothelial nitric oxide synthase and elevates blood pressure.	2008-09	18645049
Host control of malaria infections: constraints on immune and erythropoeitic response kinetics.	2008-08-22	18725923
Cellular uptake of sepiapterin and push-pull accumulation of tetrahydrobiopterin.	2008-08	18511317
A metabolomic perspective of melatonin metabolism in the mouse.	2008-04	18187545
Protective effects of melatonin and N-acetylserotonin on aflatoxin B1-induced lipid peroxidation in rats.	2008-04	17868196
Tryptophan hydroxylase is modulated by L-type calcium channels in the rat pineal gland.	2008-02-27	18221757
Melatonin formation in pineal gland from rats with hexachlorobenzene experimental porphyria.	2007-12-11	18066970
Effect of luzindole and other melatonin receptor antagonists on iron- and lipopolysaccharide-induced lipid peroxidation in vitro.	2007-12	18077581
Effect of methyl derivatives of dopamine on tumor necrosis factor alpha and lipid peroxidation.	2007-12	18077578
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.	2007-12	18077577
Neuro-endocrine correlates of ovarian development and egg-laying behaviors in the primitively eusocial wasp (Polistes chinensis).	2007-09	17451741
Photocatalytic mechanisms of indoleamine destruction by the quinalphos metabolite 2-hydroxyquinoxaline: a study on melatonin and its precursors serotonin and N-acetylserotonin.	2007-08	17701694
Analysis of melatonin using a pH- and temperature-responsive aqueous chromatography system.	2007-07-13	17292374
The effect of melatonin and structural analogues on the lipid peroxidation of triglycerides enriched in omega-3 polyunsaturated fatty acids.	2007-07-04	17603083
Melatonin and N-acetyl serotonin inhibit selectively enzymatic and non-enzymatic lipid peroxidation of rat liver microsomes.	2007-07	17681744
Effects of reserpine and p-chloroamphetamine on 5-HT metabolism and release in the cerebral ganglia of Inachis io (Lepidoptera).	2007-06	17933387
Melatonin the "light of night" in human biology and adolescent idiopathic scoliosis.	2007-04-04	17408483
Ultrastructural and hormonal changes in the pineal-testicular axis following arecoline administration in rats.	2007-04-01	17436329
N1-acetyl-N2-formyl-5-methoxykynuramine modulates the cell cycle of malaria parasites.	2007-04	17349024
Pinoline and N-acetylserotonin reduce glutamate-induced lipid peroxidation in retinal homogenates.	2007-02-02	17125922
Melatonin and its metabolites: new findings regarding their production and their radical scavenging actions.	2007	17351668
Effect of TNF-alpha on the melatonin synthetic pathway in the rat pineal gland: basis for a 'feedback' of the immune response on circadian timing.	2006-11	17014691
Melatonin inhibits endothelial nitric oxide production in vitro.	2006-10	16948788
Relationship between nocturnal serotonin surge and melatonin onset in rodent pineal gland.	2006-09-27	17005040
The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study.	2006-09	17003850
Effect of three different cultivars of Lepidium meyenii (Maca) on learning and depression in ovariectomized mice.	2006-06-23	16796734
Association between adolescent idiopathic scoliosis prevalence and age at menarche in different geographic latitudes.	2006-05-23	16759371
Preparation and identification of anti-melatonin monoclonal antibodies.	2006-05	16635023
The effects of melatonin, N-acetylserotonin, and 6-hydroxymelatonin on the ultrastructure of the pinealocytes of the Syrian hamster (Mesocricetus auratus).	2006-04-01	16575756
Folic acid reverses endothelial dysfunction induced by inhibition of tetrahydrobiopterin biosynthesis.	2006-01-20	16387296
Analysis of biogenic amine variability among individual fly heads with micellar electrokinetic capillary chromatography-electrochemical detection.	2005-11-01	16255588
Hypercholesterolemia abrogates late preconditioning via a tetrahydrobiopterin-dependent mechanism in conscious rabbits.	2005-10-04	16186416
Free-running rhythms of pineal circadian output.	2005-10	16267382
Products of tryptophan catabolism induce Ca2+ release and modulate the cell cycle of Plasmodium falciparum malaria parasites.	2005-10	16150101
Failure to respond to endogenous or exogenous melatonin may cause nonphotoresponsiveness in Harlan Sprague Dawley rats.	2005-09-14	16162292
Microcolumn separation of amine metabolites in the fruit fly.	2005-08-15	16097779
N-acetyldopamine inhibits rat brain lipid peroxidation induced by lipopolysaccharide.	2005-08	16179545
Immune-modulating effects of melatonin, N-acetylserotonin, and N-acetyldopamine.	2005-08	16179544
Antioxidant effects of N-acetylserotonin: possible mechanisms and clinical implications.	2005-08	16179540
N-acetyltransferase is not the rate-limiting enzyme of melatonin synthesis at night.	2005-08	15978063
Corticosterone modulates noradrenaline-induced melatonin synthesis through inhibition of nuclear factor kappa B.	2005-04	15725340
Protective effects of N-acetylserotonin against 6-hydroxydopamine-induced neurotoxicity.	2005-03-25	15733934
Retinal ganglion cells are autonomous circadian oscillators synthesizing N-acetylserotonin during the day.	2004-12-03	15448149
The circadian rhythm of 5-HT biosynthetic and degradative enzymes in immortalized mouse neuroendocrine pineal cell line--a model for studying circadian rhythm.	2004-11-05	15474553
Protective effect of N-acetyl-serotonin on the nonenzymatic lipid peroxidation in rat testicular microsomes and mitochondria.	2004-10	15357659
Diurnal rhythms in cocaine sensitization and in Period1 levels are common across rodent species.	2004-09	15388282

Name

Type

Language

N-ACETYLSEROTONIN

Common Name

English

5-HYDROXYMELATONIN

Preferred Name

English

ACETAMIDE, N-(2-(5-HYDROXYINDOL-3-YL)ETHYL)-

Systematic Name

English

ACETAMIDE, N-(2-(5-HYDROXY-1H-INDOL-3-YL)ETHYL)-

Systematic Name

English

NORMELATONIN

Common Name

English

N-ACETYL-2-(5-HYDROXYINDOL-3-YL)ETHYLAMINE

Systematic Name

English

N-(2-(5-HYDROXY-1H-INDOL-3-YL)ETHYL)ACETAMIDE

Systematic Name

English

5-HYDROXY-N-ACETYLTRYPTAMINE

Systematic Name

English

O-DEMETHYLMELATONIN

Common Name

English

N-ACETYL-5-HYDROXYTRYPTAMINE

Systematic Name

English

Code System Code Type Description

SMS_ID

100000140279