A2355

Sigma-Aldrich

AFMK

≥98% (HPLC), solid

Synonym(s):
N-[3-[2-(Formylamino)-5-methoxyphenyl]-3-oxopropyl]acetamide, NSC 688263
Empirical Formula (Hill Notation):
C13H16N2O4
CAS Number:
Molecular Weight:
264.28
MDL number:
PubChem Substance ID:

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

COc1ccc(NC=O)c(c1)C(=O)CCNC(C)=O

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Biochem/physiol Actions

AFMK is a melatonin metabolite first detected in rat brain; demonstrates antioxidant and free radical scavenging activities in several experimental models; inhibits LPS-mediated production of TNFα and IL-8 in neutrophils; useful tool in the study of melatonin metabolism.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

3

Certificate of Analysis
Certificate of Origin
Kailash Manda et al.
Journal of pineal research, 45(4), 430-438 (2008-07-18)
Evaluation of potential health effects from high energy charged particle radiation exposure during long duration space travel is important for the future of manned missions. Cognitive health of an organism is considered to be maintained by the capacity of hippocampal...
Natasa Dragicevic et al.
Journal of pineal research, 51(1), 75-86 (2011-03-02)
Mitochondrial dysfunction is a hallmark of Alzheimer's disease (AD) and is observed in mutant amyloid precursor protein (APP) transgenic mouse models of familial AD. Melatonin is a potent antioxidant, can prevent toxic aggregation of Alzheimer's beta-amyloid (Aβ) peptide and, when...
Valdecir F Ximenes et al.
Journal of pineal research, 42(3), 291-296 (2007-03-14)
There is a growing body of evidence that melatonin and its oxidation product, N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK), have anti-inflammatory properties. From a nutritional point of view, the discovery of melatonin in plant tissues emphasizes the importance of its relationship with plant peroxidases....
Valdecir F Ximenes et al.
Journal of pineal research, 49(2), 115-122 (2010-06-16)
Melatonin is widely known for its antioxidant, immunomodulatory, and anti-inflammatory effects. Hypochlorous acid (HOCl) is one example of an endogenous oxidant that is promptly neutralized by melatonin. Melatonin also inhibits myeloperoxidase, the enzyme that catalyzes the oxidation of chloride to...
S O Silva et al.
Journal of neuroimmunology, 156(1-2), 146-152 (2004-10-07)
A growing body of evidence suggests that the pineal hormone, melatonin, has immunomodulatory properties, although very little is known about its effect on leukocytes. Therefore, we aimed to investigate the effect of melatonin and its oxidation product N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) on...

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