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N1-Acetyl-5-methoxykynuramine

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N1-Acetyl-5-methoxykynuramine (AMK) is a metaboliteofmelatonin that could improve memory by acting on the melatonin receptors. It significantly increased the phosphorylation of both ERK and CREB in the hippocampus.^[1] It also helps scavenge free radicals.^[2]

N1-Acetyl-5-methoxykynuramine
Names

IUPAC name N-[3-(2-Amino-5-methoxyphenyl)-3-oxopropyl]acetamide
Identifiers
CAS Number	52450-39-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:173696
ChEMBL	ChEMBL369941
ChemSpider	346276
PubChem CID	UNII 3906582.3.2 UNII
CompTox Dashboard (EPA)	DTXSID10966880
InChI InChI=1S/C12H16N2O3/c1-8(15)14-6-5-12(16)10-7-9(17-2)3-4-11(10)13/h3-4,7H,5-6,13H2,1-2H3,(H,14,15) Key: RJQIZOKNUKRKTP-UHFFFAOYSA-N
SMILES CC(=O)NCCC(=O)C1=C(C=CC(=C1)OC)N
Properties
Chemical formula	C₁₂H₁₆N₂O₃
Molar mass	236.271 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

^ "Research Reveals How Melatonin Boosts Long-Term Memory". SciTechDaily. 2024-03-05. Retrieved 2024-03-11.

^ Ressmeyer, Anna-Rebekka; Mayo, Juan C.; Zelosko, Veronika; Sáinz, Rosa M.; Tan, Dun-Xian; Poeggeler, Burkhard; Antolín, Isaac; Zsizsik, Beata K.; Reiter, Russel J.; Hardeland, Rüdiger (2003). "Antioxidant properties of the melatonin metabolite N1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction". Redox Report: Communications in Free Radical Research. 8 (4): 205–213. doi:10.1179/135100003225002709. ISSN 1351-0002. PMID 14599344.

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Retrieved from "https://en.wikipedia.org/w/index.php?title=N1-Acetyl-5-methoxykynuramine&oldid=1222201114" Last edited on 4 May 2024, at 14:54

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