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SMB01350

Sigma-Aldrich

N1-Acetyl-5-methoxykynuramine

≥95% (HPLC)

Synonym(s):

N-[3-(2-Amino-5-methoxyphenyl)-3-oxopropyl]acetamide

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About This Item

Empirical Formula (Hill Notation):
C12H16N2O3
CAS Number:
52450-39-2
Molecular Weight:
236.27
MDL number:
MFCD00269871
UNSPSC Code:
12352205

Quality Level

200

Assay

≥95% (HPLC)

form

solid

mp

88—91 °C

storage temp.

2-8°C

SMILES string

NC1=C(C(CCNC(C)=O)=O)C=C(OC)C=C1

InChI

1S/C12H16N2O3/c1-8(15)14-6-5-12(16)10-7-9(17-2)3-4-11(10)13/h3-4,7H,5-6,13H2,1-2H3,(H,14,15)

InChI key

RJQIZOKNUKRKTP-UHFFFAOYSA-N

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

Other Notes

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000145301

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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
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
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

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