Pyridoxamine

Pyridoxamine

Names
IUPAC name 4-(aminomethyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol
Identifiers
CAS Number	85-87-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16410 Y
ChemSpider	1023 Y
ECHA InfoCard	100.001.491
KEGG	C00534 Y
PubChem CID	1052
UNII	6466NM3W93 N
InChI InChI=1S/C8H12N2O2/c1-5-8(12)7(2-9)6(4-11)3-10-5/h3,11-12H,2,4,9H2,1H3 Y Key: NHZMQXZHNVQTQA-UHFFFAOYSA-N Y InChI=1/C8H12N2O2/c1-5-8(12)7(2-9)6(4-11)3-10-5/h3,11-12H,2,4,9H2,1H3 Key: NHZMQXZHNVQTQA-UHFFFAOYAS
SMILES Oc1c(c(cnc1C)CO)CN
Properties
Chemical formula	C8H12N2O2
Molar mass	168.20 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Pyridoxamine is one form of vitamin B₆. Chemically it is based on a pyridine ring structure, with hydroxyl, methyl, aminomethyl, and hydroxymethyl substituents. It differs from pyridoxine by the substituent at the 4-position. The phenol at position 3 and aminomethyl group at position 4 of its ring endow pyridoxamine with a variety of chemical properties, including the scavenging of free radical species and carbonyl species formed in sugar and lipid degradation and chelation of metal ions that catalyze Amadori reactions.

Pyridoxamine can form fairly weak complexes with a number of transition metal ions, with a preference for Cu²⁺ and Fe³⁺. The 3'-hydroxyl group of pyridoxamine allows for efficient hydroxyl radical scavenging.

Pyridoxamine inhibits the Maillard reaction and can block the formation of advanced glycation endproducts, which are associated with medical complications of diabetes. Pyridoxamine is hypothesized to trap intermediates in the formation of Amadori products released from glycated proteins, possibly preventing the breakdown of glycated proteins by disrupting the catalysis of this process through disruptive interactions with the metal ions crucial to the redox reaction. One research study found that pyridoxamine specifically reacts with the carbonyl group in Amadori products, but inhibition of post-Amadori reactions (that can lead to advanced glycation endproducts) is due in much greater part to the metal chelation effects of pyridoxamine.