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A1824

Sigma-Aldrich

N-Acetyl-5-hydroxytryptamine

≥99% (HPLC), powder, antioxidant

Synonym(s):

N-Acetylserotonin, Normelatonin

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
1210-83-9
Molecular Weight:
218.25
EC Number:
214-916-5
MDL number:
MFCD00005656
UNSPSC Code:
12352209
PubChem Substance ID:
24278209
NACRES:
NA.32

product name

N-Acetyl-5-hydroxytryptamine, ≥99% (HPLC), powder

Quality Level

200

assay

≥99% (HPLC)

form

powder

color

white to faint yellow

mp

120-122 °C (lit.)

solubility

ethanol: 50 mg/mL

storage temp.

2-8°C

SMILES string

CC(=O)NCCc1c[nH]c2ccc(O)cc12

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)

InChI key

MVAWJSIDNICKHF-UHFFFAOYSA-N

Gene Information

human ... MTNR1A(4543) , MTNR1B(4544)

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General description

N-Acetylserotonin (NAS)/normelatonin acts as a precursor of melatonin in the tryptophan metabolic pathway.

Application

N-Acetyl-5-hydroxytryptamine has been used to treat neuron cells and to analyze its effects on Krüppel-like factor 15 (KLF15) expression.

Biochem/physiol Actions

N-acetyl-serotonin (NAS/normelatonin) can act as a shelter to neurons due to its protecting ability against oxidative challenges. It can also repress the actions of the transcription factor NF-kappaB. NAS possesses antioxidant and antiaging actions. It has protective action against β-amyloid induced neurotoxicity. It helps to maintain the optimal fluidity of the biological membranes.
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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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N-acetyl-serotonin (normelatonin) and melatonin protect neurons against oxidative challenges and suppress the activity of the transcription factor NF-kappaB
Lezoualch F, et al.
Journal of Pineal Research, 24(3), 168-178 (1998)
N-Acetylserotonin and 6-hydroxymelatonin against oxidative stress: Implications for the overall protection exerted by melatonin
A?lvarez DR, et al.
The Journal of Physical Chemistry B, 119(27), 8535-8543 (2015)
Gianluca Tosini et al.
The Neuroscientist : a review journal bringing neurobiology, neurology and psychiatry, 18(6), 645-653 (2012-05-16)
N-Acetylserotonin (NAS) is a naturally occurring chemical intermediate in biosynthesis of melatonin. Previous studies have shown that NAS has different brain distribution patterns from those of serotonin and melatonin, suggesting that NAS might have functions other than as a precursor
J Vanecek et al.
Endocrinology, 126(3), 1509-1513 (1990-03-01)
Melatonin's transduction mechanisms were investigated using in vitro cultured anterior hemipituitaries. Melatonin inhibited cAMP and 3',5'-cyclic GMP accumulation in neonatal rat anterior pituitary stimulated with LHRH. Maximal inhibitory effect was reached within 25 min and persisted for at least 20
Sung-Wuk Jang et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(8), 3876-3881 (2010-02-06)
Brain-derived neurotrophic factor (BDNF) is a cognate ligand for the TrkB receptor. BDNF and serotonin often function in a cooperative manner to regulate neuronal plasticity, neurogenesis, and neuronal survival. Here we show that NAS (N-acetylserotonin) swiftly activates TrkB in a
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