AFMK

Product NameAFMK
CAS52450-38-1
MFC13H16N2O4
MW264.28
EINECS
MOL File52450-38-1.mol

Chemical Properties

Melting point	138-140°C
Boiling point	589.4±50.0 °C(Predicted)
Density	1.216±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: >10 mg/mL
form	solid
pka	13.79±0.70(Predicted)
color	white
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)
InChIKey	JYWNYMJKURVPFH-UHFFFAOYSA-N
SMILES	COc1ccc(NC=O)c(c1)C(=O)CCNC(C)=O

Safety Information

Hazard Codes	T
Risk Statements	25
Safety Statements	45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

Melatonin is a neurotransmitter widely distributed in eukaryotes and is closely linked to circadean rhythms in mammals including humans. AFMK is a melatonin metabolite first identified in rat brain. AFMK has antioxidant and free radical scavenging activities in several experimental models. AFMK may also be measured in plasma as an index of melatonin synthesis and metabolism.

Chemical Properties

Light Brown Solid

Uses

A metabolite of melatonin (M215000).

Definition

ChEBI: N-gamma-Acetyl-N-2-Formyl-5-Methoxykynurenamine is an aromatic ketone.

in vivo

AFMK is a potent antioxidant in vivo. AFMK significantly reverses radiation-induced decline in the total antioxidant capacity of plasma in mice^[2].

Animal Model:	Male C57BL mice 8 wk of age^[2]
Dosage:	10 mg/kg body weight
Administration:	Intraperitoneal injection
Result:	Radiation-induced decline in the total antioxidant capacity of plasma was significantly reversed in AFMK pretreated mice. AFMK-pretreated irradiated groups showed a significantly lower value of comet tail length and % DNA in tail.

IC 50

Human Endogenous Metabolite

References

[1] F. HIRATA. In vitro and in vivo formation of two new metabolites of melatonin.[J]. The Journal of Biological Chemistry, 1974, 3 1: 1311-1313. DOI: 10.1016/s0021-9258(19)42976-1
[2] DUN-XIAN TAN. N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant[J]. FASEB Journal, 2001, 15 12: 1-16. DOI: 10.1096/fj.01-0309fje
[3] CATHERINE HARTHé . Radioimmunoassay of N-acetyl-N-formyl-5-methoxykynuramine (AFMK): a melatonin oxidative metabolite[J]. Life sciences, 2003, 73 12: Pages 1587-1597. DOI: 10.1016/s0024-3205(03)00483-1

AFMK

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MSDS

Usage And Synthesis

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