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SMB01335

Sigma-Aldrich

N1-Acetyl-N2-formyl-5-methoxykynuramine

≥95% (HPLC)

Synonym(s):

AFMK, AFMKA, NSC-688263, NSC688263, 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:
12352116
NACRES:
NA.77

Quality Level

200

Assay

≥95% (HPLC)

form

solid

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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General description

Melatonin and its metabolites are being studied for their antioxidant properties and their protective effects against oxidative stress in both mammals and in plants. N1-Acetyl-5-methoxykynuramine (AMK) and its direct precursor N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) are two metabolites that contribute to the antioxidant properties of melatonin.

Application

Metabolomics research

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

Signal Word

Danger

Hazard Statements

H301

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000381086
0000381086
0000281420
0000224977
0000210273

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Rüdiger Hardeland
Molecules (Basel, Switzerland), 22(11) (2017-11-22)
Melatonin is catabolized both enzymatically and nonenzymatically. Nonenzymatic processes mediated by free radicals, singlet oxygen, other reactive intermediates such as HOCl and peroxynitrite, or pseudoenzymatic mechanisms are not species- or tissue-specific, but vary considerably in their extent. Higher rates of
Kyoungwhan Back
The Plant journal : for cell and molecular biology, 105(2), 376-391 (2020-07-10)
Melatonin is a multifunctional biomolecule found in both animals and plants. In this review, the biosynthesis, levels, signaling, and possible roles of melatonin and its metabolites in plants is summarized. Tryptamine 5-hydroxylase (T5H), which catalyzes the conversion of tryptamine into
Hikaru Iwashita et al.
Journal of pineal research, 70(1), e12703-e12703 (2020-10-31)
Melatonin (MEL) has been reported to enhance cognitive processes, making it a potential treatment for cognitive decline. However, the role of MEL's metabolites, N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) and N1-acetyl-5-methoxykynuramine (AMK), in these effects are unknown. The current study directly investigated the acute

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