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N1-Acetyl-5-methoxykynuramine

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Metabolite of melatonin


N1-Acetyl-5-methoxykynuramine
Names
IUPAC name N-acetamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

N1-Acetyl-5-methoxykynuramine (AMK) is a metabolite of melatonin that could improve memory by acting on the melatonin receptors. AMK is produced from the metabolization of melatonin by the kynuramine pathway in the brain. It significantly increased the phosphorylation of both ERK and CREB in the hippocampus. It also helps scavenge free radicals. AMK is highly reactive towards dioxygen (O2) radicals because of AMK's Namino group.

References

  1. Watanabe, Kazuki; Hattori, Atsuhiko (June 2025). "Aging-induced memory loss due to decreased N1-acetyl-5-methoxykynuramine, a melatonin metabolite, in the hippocampus: a potential prophylactic agent for dementia". Neural Regeneration Research. 20 (6): 1705. doi:10.4103/NRR.NRR-D-24-00379. ISSN 1673-5374. PMC 11688570. PMID 39104103.
  2. "Research Reveals How Melatonin Boosts Long-Term Memory". SciTechDaily. 2024-03-05. Retrieved 2024-03-11.
  3. 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.
  4. Schaefer, Meike; Hardeland, Rüdiger (2009). "The melatonin metabolite N1-acetyl-5-methoxykynuramine is a potent singlet oxygen scavenger". Journal of Pineal Research. 46 (1): 49–52. doi:10.1111/j.1600-079X.2008.00614.x. ISSN 1600-079X. PMID 18643875.


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