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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:
52450-38-1
Molecular Weight:
264.28
MDL number:
MFCD02683241
UNSPSC Code:
12352200
PubChem Substance ID:
24724387

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
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
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
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
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