pyridoxamine
pyridoxamine Basic information
- Product Name:
- pyridoxamine
- Synonyms:
-
- 4-(azaniumylmethyl)-5-(hydroxymethyl)-2-methylpyridin-3-olate
- 4-(aminomethyl)-5-(hydroxymethyl)-2-methyl-pyridin-3-ol
- 3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinemethanamine
- 4-Aminomethyl-5-hydroxy-6-methyl-3-pyridinemethanol
- Pyridorin
- 4-(aminomethyl)-2-methyl-5-methylol-pyridin-3-ol
- PyridoxaMine-d4
- Pyridoxylamine
- CAS:
- 85-87-0
- MF:
- C8H12N2O2
- MW:
- 168.19
- EINECS:
- 201-640-5
- Mol File:
- 85-87-0.mol
pyridoxamine Chemical Properties
- Melting point:
- 193-193.5 °C
- Boiling point:
- 460.1±40.0 °C(Predicted)
- Density
- 1.282±0.06 g/cm3(Predicted)
- storage temp.
- Hygroscopic, Refrigerator, under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.98±0.10(Predicted)
- color
- Pale Yellow
- Stability:
- Hygroscopic
pyridoxamine Usage And Synthesis
Uses
Pyridoxylamine is an advanced glycation end production (AGEs) and lipoxidation end products (ALEs) inhibitor, to protect against diabetes-induced retinal vascular lesions.
Definition
ChEBI: Pyridoxamine is a monohydroxypyridine that is pyridine substituted by a hydroxy group at position 3, an aminomethyl group at position 4, a hydroxymethyl group at position 5 and a methyl group at position 2. The 4-aminomethyl form of vitamin B6, it is used (in the form of the hydrochloride salt) for treatment of diabetic nephropathy. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a plant metabolite, a mouse metabolite, an iron chelator and a nephroprotective agent. It is a hydroxymethylpyridine, a monohydroxypyridine, an aminoalkylpyridine and a vitamin B6. It is a conjugate base of a pyridoxaminium(1+).
in vivo
Pyridoxylamine limits the formation of CML and CEL and cross-linking in skin collagen and, ultimately inhibits the development of nephropathy in STZ-diabetic rats. Pyridoxylamine does not appear to function as an antioxidant since it does not prevent lipid peroxidation reactions. At the same time, it does prevent protein modification by products of lipid peroxidation, including inhibiting formation of malondialdehyde and 4-hydroxynonenal adducts on protein in Zucker rats in vivo[1].
IC 50
Human Endogenous Metabolite
References
[1] Stitt A, et al. The AGE inhibitor pyridoxamine inhibits development of retinopathy in experimental diabetes. Diabetes. 2002 Sep;51(9):2826-32. DOI:10.2337/diabetes.51.9.2826
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