>>Signaling Pathways>> Ox Stress Reagents>> Lipid Peroxidation>>AMK (hydrochloride)

AMK (hydrochloride) (Synonyms: N-γ-acetyl-5-Methoxykynurenamine, N1-acetyl-5-Methoxykynuramine)

Catalog No.GC49336

An active metabolite of melatonin

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AMK (hydrochloride) Chemical Structure

Cas No.: 1215711-91-3

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1 mg
US$60.00
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5 mg
US$255.00
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10 mg
US$479.00
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Sample solution is provided at 25 µL, 10mM.

Description of AMK (hydrochloride)

AMK is an active metabolite of the neurohormone melatonin .1,2,3,4 It is formed from melatonin via the metabolic intermediate AFMK 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 and PGD2 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

1.Schaefer, M., and Hardeland, R.The melatonin metabolite N1-acetyl-5-methoxykynuramine is a potent singlet oxygen scavengerJ. 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 biosynthesisBiochem. 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 macrophagesJ. 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 miceJ. 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 biotransformationFree 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 melatoninJ. Biol. Chem.249(4)1311-1313(1974)

Chemical Properties of AMK (hydrochloride)

Cas No. 1215711-91-3 SDF
Synonyms N-γ-acetyl-5-Methoxykynurenamine, N1-acetyl-5-Methoxykynuramine
Canonical SMILES O=C(C)NCCC(C1=CC(OC)=CC=C1N)=O.Cl
Formula C12H16N2O3·HCl M.Wt 272.7
Solubility Methanol: slightly soluble,Water: slightly soluble Storage -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of AMK (hydrochloride)

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1 mg 5 mg 10 mg
1 mM 3.667 mL 18.3352 mL 36.6703 mL
5 mM 0.7334 mL 3.667 mL 7.3341 mL
10 mM 0.3667 mL 1.8335 mL 3.667 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 33 reference(s) in Google Scholar.)

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