N1-Acetyl-5-methoxykynuramine (hydrochloride)

N1-Acetyl-5-methoxykynuramine (AMK) hydrochloride is an active metabolite of the neurohormone melatonin (HY-B0075) . N1-Acetyl-5-methoxykynuramine hydrochloride (200 µM) effectively scavenges singlet oxygen (ROS) .1 It also inhibits the production of prostaglandin E2 (PGE2) and prostaglandin D2 (PGD2) induced by epinephrine and arachidonic acid in a concentration- and time-dependent manner, and suppresses the increase in COX-2 levels induced by LPS (HY-D1056) in RAW 264.7 macrophages at a concentration of 500 µM. In a mouse model of Parkinson's disease induced by MPTP (HY-15608), N1-Acetyl-5-methoxykynuramine hydrochloride (20 mg/kg) reduces the increase in lipid peroxidation in the cytosol and mitochondria of the substantia nigra and striatum. N1-Acetyl-5-methoxykynuramine hydrochloride can be used in research on metabolic and neurological diseases[1][2][3][4][5][6]

Product Specifications

CAS Number

[1215711-91-3]

Product Name Alternative

AMK (hydrochloride)

UNSPSC

12352005

Hazard Statement

H302-H361

Target

COX; PGE synthase; Prostaglandin Receptor; Reactive Oxygen Species (ROS)

Related Pathways

GPCR/G Protein; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB

Field of Research

Metabolic Disease; Neurological Disease

Smiles

O=C(C)NCCC(C1=CC(OC)=CC=C1N)=O.Cl

Molecular Formula

C12H17ClN2O3

Molecular Weight

272.73

Precautions

P264-P270-P280-P330-P405-P501

References & Citations

[1]Hirata F, et al. In vitro and in vivo formation of two new metabolites of melatonin. J Biol Chem. 1974 Feb 25;249 (4) :1311-3.|[2]Schaefer M, et al. The melatonin metabolite N-acetyl-5-methoxykynuramine is a potent singlet oxygen scavenger. J Pineal Res. 2009 Jan;46 (1) :49-52.|[3]Kelly RW, et al. N-acetyl-5-methoxy kynurenamine, a brain metabolite of melatonin, is a potent inhibitor of prostaglandin biosynthesis. Biochem Biophys Res Commun. 1984 May 31;121 (1) :372-9.|[4]Mayo JC, 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. 2005 Aug;165 (1-2) :139-49.|[5]Tapias V, et al. Melatonin and its brain metabolite N (1) -acetyl-5-methoxykynuramine prevent mitochondrial nitric oxide synthase induction in parkinsonian mice. J Neurosci Res. 2009 Oct;87 (13) :3002-10. |[6]Tan DX, et al. Melatonin directly scavenges hydrogen peroxide: a potentially new metabolic pathway of melatonin biotransformation. Free Radic Biol Med. 2000 Dec;29 (11) :1177-85.