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Merck
CN

A2355

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
UNSPSC Code:
12352200
PubChem Substance ID:
24724387
MDL number:
MFCD02683241

Key Documents

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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)

SMILES string

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

InChI key

JYWNYMJKURVPFH-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL, H2O: insoluble

storage temp.

2-8°C

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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
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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
087K46163
087K46162
087K46161
087K4616
075K4615

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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
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
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
Fabrice Collin et al.
Journal of mass spectrometry : JMS, 44(3), 318-329 (2008-11-19)
The hydrogen-deuterium exchange of protonated melatonin and its in vitro oxidation end-products have been examined by liquid chromatography coupled with ion-trap mass spectrometry. Specific H/D scrambling of protons in the C2 and C4 positions of the indole ring during gas-phase
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