N-Acetylserotonin

Names

[ Name ]:
N-Acetylserotonin

[Synonym ]:
EINECS 214-916-5
N-acetyl-5-HT
N-Acetylserotonin
3-(2-Acetamidoethyl)-5-hydroxyindole
Serotonin, N-acetyl-
Normelatonin
N-Acetylserotonin,Normelatonin
Acetamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-
N-Acetylserotonin Normelatonin
N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]acetamide
N-Acetyl-5-hydroxytryptamine
N-acetyl-serotonin
MFCD00005656
5-Hydroxymelatonin
5-Hydroxy-N-acetyltryptamine
N-ACETYL SEROTONIN

Biological Activity

[Description]:

N-Acetyl-5-hydroxytryptamine is a Melatonin precursor, and that it can potently activate TrkB receptor.

[Related Catalog]:

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> Trk Receptor

Research Areas >> Neurological Disease

Natural Products >> Others

[Target]

Human Endogenous Metabolite

TrkB

[In Vitro]

N-Acetyl-5-hydroxytryptamine (NAS), a precursor of Melatonin, is acetylated from serotonin by AANAT (arylalkylamine N-acetyltransferase). N-acetylserotonin activates TrkB receptor in a circadian rhythm. N-Acetyl-5-hydroxytryptamine swiftly activates TrkB in a circadian manner and exhibits antidepressant effect in a TrkB-dependent manner. N-Acetyl-5-hydroxytryptamine rapidly activates TrkB, but not TrkA or TrkC, in a neurotrophin- and MT3 receptor-independent manner[1].

[In Vivo]

To explore whether N-Acetyl-5-hydroxytryptamine, can trigger TrkB activation in vivo, TrkB F616A knockin mice are employed, where it has been shown that TrkB F616A activation can be selectively blocked by 1NMPP1, a derivative of kinase inhibitor PP1, leading to TrkB-null phenotypes. To assess whether N-Acetyl-5-hydroxytryptamine can mimic BDNF, cortical neurons from TrkB F616A knockin mice are prepared. In alignment with a previous report, BDNF- and NAS-mediated TrkB phosphorylation are selectively reduced by 1NMPP1 but not by K252a, whereas serotonin or Melatonin had no effect . These findings suggest that NAS strongly provokes both wild-type TrkB and TrkB F616A tyrosine phosphorylation and activation[1].

[Animal admin]

Mice[1] Two-month-old TrkB F616A mice are pretreated with 1NMPP1 in drinking water (50 μM) 1 day before the experiment, followed by administration of N-Acetyl-5-hydroxytryptamine (20 mg/kg, i.p.) or Melatonin (1 mg/kg, i.p.). Mice are killed at 1 h. The brain homogenates are analyzed by immunoblotting with anti-p-TrkB. Two- to three-month-old BDNF forebrain conditional knockout mice are injected i.p. with N-Acetyl-5-hydroxytryptamine or Melatonin. Mice are killed at 0, 0.5, 1, or 2 h following drug administration. Brain lysates are prepared and analyzed by immunoblotting with anti-phospho-TrkB Y816[1].

[References]

[1]. Jang SW, et al. N-acetylserotonin activates TrkB receptor in a circadian rhythm. Proc Natl Acad Sci U S A. 2010 Feb 23;107(8):3876-81.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
556.8±40.0 °C at 760 mmHg

[ Melting Point ]:
120-122 °C(lit.)

[ Molecular Formula ]:
C₁₂H₁₄N₂O₂

[ Molecular Weight ]:
218.252

[ Flash Point ]:
290.6±27.3 °C

[ Exact Mass ]:
218.105530

[ PSA ]:
65.12000

[ LogP ]:
-0.13

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.651

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
ethanol: 50 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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