A2355

Sigma-Aldrich

AFMK

≥98% (HPLC), solid

Synonym(s):
N-[3-[2-(Formylamino)-5-methoxyphenyl]-3-oxopropyl]acetamide, NSC 688263
Empirical Formula (Hill Notation):
C13H16N2O4
CAS Number:
Molecular Weight:
264.28
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

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

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

25

Safety Statement

45

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

3

Certificate of Analysis
Certificate of Origin
Rüdiger Hardeland et al.
Journal of pineal research, 47(2), 109-126 (2009-07-04)
Kynuramines represent their own class of biogenic amines. They are formed either by decarboxylation of kynurenines or pyrrole ring cleavage of indoleamines. N(2)-formylated compounds formed in this last reaction can be deformylated either enzymatically by arylamine formamidases or hemoperoxidases, or...
Valdecir F Ximenes
Journal of pineal research, 45(3), 297-301 (2008-04-01)
N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK) is the product of oxidative pyrrole ring cleavage of melatonin. AFMK and its deformylated derivative N(1)-acetyl-5-methoxykynuramine (AMK) are compounds for which there are increasing demands because of their antioxidant, immunomodulatory and anti-inflammatory properties. Here, we sought to determine...
S O Silva et al.
Journal of neuroimmunology, 156(1-2), 146-152 (2004-10-07)
A growing body of evidence suggests that the pineal hormone, melatonin, has immunomodulatory properties, although very little is known about its effect on leukocytes. Therefore, we aimed to investigate the effect of melatonin and its oxidation product N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) on...
Catherine Harthé et al.
Life sciences, 73(12), 1587-1597 (2003-07-17)
N-acetyl-N-formyl-5-methoxykynuramine (AFMK) is a melatonin metabolite identified in rat brain by Hirata et al. (The Journal of Biological Chemistry 249 (1974) 1311). Since no assay has been described for its routine measurement, we have developed and validated such a radioimmunoassay....
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...

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