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Merck
CN

A2355

Sigma-Aldrich

AFMK

≥98% (HPLC), solid

Synonym(s):

N-[3-[2-(Formylamino)-5-methoxyphenyl]-3-oxopropyl]acetamide, NSC 688263

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About This Item

Empirical Formula (Hill Notation):
C13H16N2O4
CAS Number:
Molecular Weight:
264.28
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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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

InChI

1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)

InChI key

JYWNYMJKURVPFH-UHFFFAOYSA-N

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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.
AFMK is a melatonin oxidation product.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Kailash Manda et al.
Journal of pineal research, 42(4), 386-393 (2007-04-19)
Antioxidant function of melatonin is well established. However, N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK), a melatonin metabolite is a sparingly investigated biogenic amine, especially in relation to its in vivo antioxidant function. We have evaluated the oxidative damage to biomolecules (DNA, protein and lipid)
Alexandre Budu et al.
Journal of pineal research, 42(3), 261-266 (2007-03-14)
We previously reported that intraerythrocytic malaria parasites have their development synchronized by melatonin and other products of tryptophan catabolism (i.e. serotonin, N-acetylserotonin and tryptamine). Here, we show that N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK), a product of melatonin degradation, synchronizes Plasmodium chabaudi and Plasmodium
Márcio Alberto Geihs et al.
General and comparative endocrinology, 166(1), 72-82 (2009-10-13)
In vertebrates, many studies verified different effects of melatonin in the antioxidant defense system (ADS). In crustaceans, few studies have been conducted to verify this possibility. We verified the melatonin effects in the crab Neohelice granulata using low (0.002 and
Valdecir F Ximenes et al.
Journal of pineal research, 44(2), 115-120 (2008-02-22)
Accumulating evidence points to relationships between increased production of reactive oxygen or decreased antioxidant protection in schizophrenic patients. Chlorpromazine (CPZ), which remains a benchmark treatment for people with schizophrenia, has been described as a pro-oxidant compound. Because the antioxidant compound
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

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