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N-Acetyl-5-hydroxytryptamine

Name: <I>N</I>-Acetyl-5-hydroxytryptamine
Brand: SIGMA

≥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

NACRES:

NA.32

PubChem Substance ID:

24278209

UNSPSC Code:

12352209

EC Number:

214-916-5

MDL number:

MFCD00005656

Assay:

≥99% (HPLC)

Form:

powder

Quality level:

200

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Properties

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)

Description

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

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.

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.

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This Item	M1514	A6251	SML2058
Sigma-Aldrich A1824 N-Acetyl-5-hydroxytryptamine	Sigma-Aldrich M1514 Nω-Methyl-5-hydroxytryptamine oxalate salt	Sigma-Aldrich A6251 N-Acetyl-DL-tryptophan	Sigma-Aldrich SML2058 5,7-Dihydroxytryptamine hydrobromide
assay ≥99% (HPLC)	assay ≥90% (HPLC)	assay ≥98% (TLC)	assay ≥94% (HPLC)
form powder	form -	form powder	form powder
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level -
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility ethanol: 50 mg/mL	solubility -	solubility -	solubility H₂O: 2 mg/mL, clear
color white to faint yellow	color -	color -	color white to dark brown

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

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: neuroprotection, neurogenesis, and the sleepy brain.

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

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Global Trade Item Number

SKU	GTIN
A1824-100MG	04061833343036
A1824-1G	04061826687697

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