N1-Acetyl-5-methoxykynuramine

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N1-Acetyl-5-methoxykynuramine
N1-Acetyl-5-methoxykynuramine.svg
Names
IUPAC name
N-[3-(2-Amino-5-methoxyphenyl)-3-oxopropyl]acetamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • 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]

Contents

Anti-inflammatory activity

Studies have shown that melatonin, along with its metabolites N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) and N1-acetyl-5-methoxykynuramine (AMK), can suppress the activation of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase(iNOS). This leads to reduced production of prostaglandin E₂ (PGE₂) and nitric oxide, respectively. COX-2 is a key enzyme involved in inflammation and its activation is triggered by lipopolysaccharide (LPS) in macrophages. Elevated levels of COX-2 expression have been linked to various disorders, such as cancer and neurodegeneration. COX-2 and iNOS are identified as newly recognized molecular targets and this supports the possible therapeutic role of melatonin, AFMK, and AMK in managing inflammatory responses. [5]

Antiproliferative effects in the human epidermis

AMK is naturally synthesized in the human skin and its concentration varies depending on the degree of melanin pigmentation. It has been shown to reduce cell proliferation in keratinocytes and cancerous melanocytes. When epidermal melanocytes and melanoma cells were cultured with AMK, a decrease in cell count was observed compared to cells exposed only to the control treatment. Studies have shown that these antiproliferative effects were maintained even when AMK is administered in the presence of L-tyrosine. [6]

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.
  5. ↑ Mayo, Juan C.; Sainz, Rosa M.; Tan, Dun-Xian; Hardeland, Rüdiger; Leon, Josefa; Rodriguez, Carmen; Reiter, Russel J. (August 2005). "Anti-inflammatory actions of melatonin and its metabolites, N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) and N1-acetyl-5-methoxykynuramine (AMK), in macrophages" . Journal of Neuroimmunology. 165 (1–2): 139–149. doi:10.1016/j.jneuroim.2005.05.002.
  6. ↑ Kim, Tae-Kang; Lin, Zongtao; Li, Wei; Reiter, Russel J.; Slominski, Andrzej T. (2015-05-01). "N 1-Acetyl-5-Methoxykynuramine (AMK) Is Produced in the Human Epidermis and Shows Antiproliferative Effects". Endocrinology. 156 (5): 1630–1636. doi:10.1210/en.2014-1980. ISSN   0013-7227. PMC   4398766 . PMID   25679869.
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