Acetyl-N-formyl-5-methoxykynurenamine

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Acetyl-N-formyl-5-methoxykynurenamine
2D structure for Acetyl-N-formyl-5-methoxykynurenamine
Chemical Name	N-[3-(2-formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide
Chemical Formula	C₁₃H₁₆N₂O₄
CAS Number	52450-38-1
Chemical Information	HMDB04259
Biochemical Taxonomy	Amino Ketones
Functional Taxonomy	Not Available
Nutritional Taxonomy	Not Available
Metabolic Pathways	Not Available
Biofluid Location	Blood Cerebrospinal Fluid (CSF)
Tissue Location	Not Available
Normal Biofluid Concentrations	Blood: 0.000065 (0.000059-0.00189) umol/L Cerebrospinal Fluid (CSF): uM
Normal Tissue Concentrations	Not Available
Diseases / Conditions Related to Nutrition	Viral meningitis
Other (Monogenic Disorders)	Not Available
Abnormal Biofluid Concentrations	Cerebrospinal Fluid (CSF) (Viral meningitis): 0.28 (0.06-0.50) uM
Abnormal Tissue Concentrations	Not Available
Physiological Processes	Not Available

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Introduction

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Acetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O )-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a specie formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration, with AFMK found in some patients exceeding the concentration of melatonin normally found in serum. (PMID 16150112)