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A1824

Sigma-Aldrich

N-Acetyl-5-hydroxytryptamine

≥99% (HPLC), powder, antioxidant

Sinonimo/i:

N-Acetylserotonin, Normelatonin

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CHF 241.00

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CHF 241.00

About This Item

Formula empirica (notazione di Hill):
C12H14N2O2
Numero CAS:
1210-83-9
Peso molecolare:
218.25
Numero CE:
214-916-5
Numero MDL:
MFCD00005656
Codice UNSPSC:
12352209
ID PubChem:
24278209
NACRES:
NA.32

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Nome del prodotto

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

Livello qualitativo

200

Saggio

≥99% (HPLC)

Stato

powder

Colore

white to faint yellow

Punto di fusione

120-122 °C (lit.)

Solubilità

ethanol: 50 mg/mL

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
MVAWJSIDNICKHF-UHFFFAOYSA-N

Informazioni sul gene

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

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Descrizione generale

N-Acetylserotonin (NAS)/normelatonin acts as a precursor of melatonin in the tryptophan metabolic pathway.[1]

Applicazioni

N-Acetyl-5-hydroxytryptamine has been used to treat neuron cells and to analyze its effects on Krüppel-like factor 15 (KLF15) expression.[2]

Azioni biochim/fisiol

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.[3] 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.[1]
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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
0000395808
0000361399
0000395808
0000361399
0000187696

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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
C S Pang et al.
Biological signals, 4(6), 311-324 (1995-11-01)
We have compared the pharmacological characteristics of 2-[125I]iodomelatonin binding to crude membrane preparations of the lung, spleen, brain and kidney of chicken. Saturation studies indicated significant differences (p < 0.05) in the equilibrium dissociation constant (Kd) and maximum number of
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