N-ACETYL-5-HYDROXYTRYPTAMINE Chemical Properties

Melting point:

120-122 °C (lit.)

Boiling point:

556.8±40.0 °C(Predicted)

Density 

1.268±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

ethanol: 50 mg/mL

form 

powder

pka

10.09±0.40(Predicted)

color 

white

Stability:

Hygroscopic

CAS DataBase Reference

1210-83-9(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

N-ACETYL-5-HYDROXYTRYPTAMINE Usage And Synthesis

Chemical Properties

white to off-white or slightly pink powder

Uses

A metabolite of Melatonin (M215000).

Uses

N-Acetyl-5-hydroxytryptamine has been used to treat neuron cells and to analyze its effects on?Krüppel-like factor 15 (KLF15) expression.

Definition

ChEBI: A member of the class of hydroxyindoles that is the N-acetyl derivative of serotonin.

General Description

N-Acetylserotonin (NAS)/normelatonin acts as a precursor of melatonin in the tryptophan metabolic pathway.

Biological Activity

n-acetylserotonin is an agonist at the melatonin receptors mt1, mt2, and mt3.a melatonin receptor is a g protein-coupled receptor binding melatonin. three types of melatonin receptor have been identified. the mt1 and mt2 receptor subtypes are in humans and other mammals, whereas an additional melatonin receptor subtype mt3 has been identified in amphibia and birds.

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.

in vitro

n-acetylserotonin, a precursor of melatonin, was acetylated from serotonin by arylalkylamine nacetyltransferase (aanat). n-acetylserotonin was found to be able to swiftly activate trkb in a circadian manner. n-acetylserotonin also exhibited antidepressant effect in a trkb-dependent manner. in additioin, n-acetylserotonin could rapidly activate trkb, but not trka or trkc, in a neurotrophin- and mt3 receptor-independent manner. moreover, n-acetylserotonin, but not melatonin, showed a robust antidepressant-like behavioral effect in a trkb-dependent way [1].

in vivo

animal study found that in bdnf knockout mice the administration of n-acetylserotonin could activate trkb. moreover, the endogenous trkb was activated in wild-type c3h/f+/+ mice but not in aanat-mutated c57bl/6j mice, in a circadian rhythm. in addition, trkb activation was found to be high at night in the dark and low during the day [1].

References

[1] jang, s. w.,liu, x.,pradoldej, s., et al. n-acetylserotonin activates trkb receptor in a circadian rhythm. proceedings of the national academy of sciences of the united states of america 107(8), 3876-3881 (2010).

N-ACETYL-5-HYDROXYTRYPTAMINE(1210-83-9)Related Product Information

• Melatonine
• 6-HYDROXYMELATONIN
• N-ACETYL-5-HYDROXYTRYPTAMINE
• Tryptamine
• 5-Hydroxytryptamine
• 5-Hydroxyindole
• N-PROPIONYL-5-METHOXYTRYPTAMINE
• N-ACETYL-5-ACETOXYTRYPTAMINE
• 6-CHLOROMELATONIN
• N-ACETYL-5-BENZYLOXYTRYPTAMINE
• N-ACETYL-5-BENZYLOXY-DL-TRYPTOPHAN
• 2-IODOMELATONIN
• N-ACETYLTRYPTAMINE
• N-ACETYL-5-HYDROXYTRYPTAMINE
• ACETAMIDE, 2-CHLORO-N-[2-(5-METHOXY-1H-INDOL-3-YL)ETHYL]-
• ACETYL-5-METHOXYTRYPTAMINE, N-[AMINOETHYL-2-3H]-
• 2-[2-(5-METHOXY-1H-INDOL-3-YL)-ETHYL]-ISOINDOLE-1,3-DIONE
• ACETYL-5'-METHOXYTRYPTAMINE, N-[METHOXY-3H]