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Merck

A1824

Sigma-Aldrich

N-Acetyl-5-hydroxytryptamine

≥99% (HPLC), powder, antioxidant

Sinónimos:

N-Acetylserotonin, Normelatonin

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About This Item

Fórmula empírica (notación de Hill):
C12H14N2O2
Número de CAS:
Peso molecular:
218.25
Número CE:
Número MDL:
Código UNSPSC:
12352209
ID de la sustancia en PubChem:
NACRES:
NA.32

product name

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

Nivel de calidad

Análisis

≥99% (HPLC)

formulario

powder

color

white to faint yellow

mp

120-122 °C (lit.)

solubilidad

ethanol: 50 mg/mL

temp. de almacenamiento

2-8°C

cadena SMILES

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)

Clave InChI

MVAWJSIDNICKHF-UHFFFAOYSA-N

Información sobre el gen

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Descripción general

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

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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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
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
Jimo Borjigin et al.
Molecular and cellular endocrinology, 349(1), 13-19 (2011-07-26)
The pineal gland is a neuroendocrine organ of the brain. Its main task is to synthesize and secrete melatonin, a nocturnal hormone with diverse physiological functions. This review will focus on the central and pineal mechanisms in generation of mammalian
KLF15 regulates dopamine D2 receptor and participates in mouse models of neuropathic pain.
Junfei Z, et al.
Biochemical and Biophysical Research Communications, 492(2), 269-274 (2017)

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