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:
Molecular Weight:
218.25
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
214-916-5
MDL number:
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
Gene Information
human ... MTNR1A(4543), MTNR1B(4544)
Related Categories
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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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
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)
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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