N1-Acetyl-5-methoxykynuramine


N1-Acetyl-5-methoxykynuramine
Names
IUPAC name
N-[3-(2-Amino-5-methoxyphenyl)-3-oxopropyl]acetamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • 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
  • CC(=O)NCCC(=O)C1=C(C=CC(=C1)OC)N
Properties
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).

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.[1] It significantly increased the phosphorylation of both ERK and CREB in the hippocampus.[2] It also helps scavenge free radicals.[3]AMK is highly reactive towards dioxygen (O2) radicals because of AMK's N2-amino group.[4]

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. 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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