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Merck
CN

A1824

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
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

Key Documents

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Product Name

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

InChI key

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)

SMILES string

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

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

Quality Level

200

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000486011
0000486011
0000395808
0000361399
0000395808

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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)
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
J K Yao et al.
Molecular psychiatry, 15(9), 938-953 (2009-04-30)
Schizophrenia is characterized by complex and dynamically interacting perturbations in multiple neurochemical systems. In the past, evidence for these alterations has been collected piecemeal, limiting our understanding of the interactions among relevant biological systems. Earlier, both hyper- and hyposerotonemia were
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