N1-Acetyl-5-methoxykynuramine hydrochloride  (Synonyms: AMK 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]}

272.73

C₁₂H₁₇ClN₂O₃

1215711-91-3

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

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]