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
Quality Level
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)
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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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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| A1824-100MG | 04061833343036 |
| A1824-1G | 04061826687697 |