An active metabolite of melatonin
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Parent Compound(s)
10005254AFMK 14427Melatonin
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AMK (hydrochloride)

Item No. 34688

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[3-(2-amino-5-methoxyphenyl)-3-oxopropyl]-acetamide, monohydrochloride
CAS Number
1215711-91-3
Synonyms
  • N-γ-acetyl-5-Methoxykynurenamine
  • N1-acetyl-5-Methoxykynuramine
Molecular Formula
C12H16N2O3 • HCl
Formula Weight
272.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: slightly solubleWater: slightly soluble
SMILES
O=C(C)NCCC(C1=CC(OC)=CC=C1N)=O.Cl
InChi Code
InChI=1S/C12H16N2O3.ClH/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);1H
InChi Key
JMBYMENFYWCJRD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    AMK is an active metabolite of the neurohormone melatonin (Item No. 14427).1,2,3,4 It is formed from melatonin via the metabolic intermediate AFMK (Item No. 10005254) that is then deformylated by catalase or formamidase.5,6 AMK scavenges singlet oxygen in vitro when used at a concentration of 200 µM.1 It inhibits the epinephrine- and arachidonic acid-induced production of prostaglandin E2 (PGE2; Item No. 14010) and PGD2 (Item No. 12010) in ovine seminal vesicle microsomes in a concentration- and time-dependent manner, as well as LPS-induced increases in COX-2 levels in RAW 264.7 macrophages when used at a concentration of 500 µM.2,3 AMK (20 mg/kg) decreases MPTP-induced increases in lipid peroxidation in the cytosol and mitochondria from substantia nigra and striatum in a mouse model of MPTP-induced Parkinson’s disease.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schaefer, M., and Hardeland, R. The melatonin metabolite N1-acetyl-5-methoxykynuramine is a potent singlet oxygen scavenger. J. Pineal Res. 46(1), 49-52 (2009).

    2. Kelly, R.W., Amato, F., and Seamark, R.F. N-acetyl-5-methoxy kynurenamine, a brain metabolite of melatonin, is a potent inhibitor of prostaglandin biosynthesis. Biochem. Biophys. Res. Commun. 121(1), 372-379 (1984).

    3. Mayo, J.C., Sainz, R.M., Tan, D.-X., et al. Anti-inflammatory actions of melatonin and its metabolites, N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) and N1-acetyl-5-methoxykynuramine (AMK), in macrophages. J. Neuroimmunol. 165(1-2), 139-149 (2005).

    4. Tapias, V., Escames, G., López, L.C., et al. Melatonin and its brain metabolite N1-acetyl-5-methoxykynuramine prevent mitochondrial nitric oxide synthase induction in parkinsonian mice. J. Neurosci. Res. 87(13), 3002-3010 (2009).

    5. Tan, D.-X., Manchester, L.C., Reiter, R.J., et al. Melatonin directly scavenges hydrogen peroxide: A potentially new metabolic pathway of melatonin biotransformation. Free Radic. Biol. Med. 29(11), 1177-1185 (2000).

    6. Hirata, F., Hayaishi, O., Tokuyama, T., et al. In vitro and in vivo formation of two new metabolites of melatonin. The Journal of Biological Chemisty 249(4), 1311-1313 (1974).