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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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
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
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)
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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