Pyridoxamine

HCID 1052CAS 85-87-0
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Basic information

Standard SMILES
Cc1ncc(CO)c(CN)c1O
InChIKey
NHZMQXZHNVQTQA-UHFFFAOYSA-N
Molecular formula
C8H12N2O2
Average molar mass
168.19 g/mol
Monoisotopic mass
168.08987763

Names & identifiers

Preferred name
Pyridoxamine
IUPAC
4-(aminomethyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol
English name
pyridoxamine
Molecular formula
C8H12N2O2
Molecular weight
168.19

Names & synonyms

pyridoxamine85-87-0Pyridoxylamine4-(AMINOMETHYL)-5-(HYDROXYMETHYL)-2-METHYLPYRIDIN-3-OL3-Pyridinemethanol, 4-(aminomethyl)-5-hydroxy-6-methyl-CHEBI:16410DTXSID60469296466NM3W93RefChem:177725DTXCID40269294-(azaniumylmethyl)-5-(hydroxymethyl)-2-methylpyridin-3-olate201-640-5
Show more names
PyridorinPyridoxaMine-d4pyridoxamine USP/EP/BPPyridoxylamine, 10 mM in DMSO4-(aminomethyl)-2-methyl-5-methylol-pyridin-3-ol4-Aminomethyl-5-hydroxy-6-methyl-3-pyridinemethanolinhibit,Inhibitor,Pyridoxylamine,Endogenous Metabolite4-(aminomethyl)-5-(hydroxymethyl)-2-methyl-pyridin-3-ol
4-(Aminomethyl)-5-(hydroxymethyl)-2-methyl-3-pyridinolEINECS 201-640-5MFCD00464815NCIStruc1_000457NCIStruc2_000537Oprea1_400404CBDivE_013510NCI21278

Database identifiers

CAS
85-87-0
PubChem CID
1052
DTXSID
DTXSID6046929
ChEMBL
CHEMBL593019
ChEBI
CHEBI:16410
UNII
6466NM3W93
EC Number
201-640-5
Nikkaji
J3.891A

Properties

Computed structural properties

XLogP
-1
Topological polar surface area
79.4 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
12

Experimental & physicochemical properties

Solubility815 mg/mL
Physical DescriptionSolid
Ionization Efficiency · 6 items

Positive

2.96

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Dissociation Constants10.34
Kovats Retention Index2000
Collision Cross Section · 5 items

140.12 Ų [M-H]- [CCS Type: DT; Method: stepped-field]；135.79 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]；148.49 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

144.1 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；133.9 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；133.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

134 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

130 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]

134.4 Ų [M+H]+；145.7 Ų [M+Na]+；136.4 Ų [M-H]-

Physicochemical properties

Melting point
193 · 193-193.5 °C
Boiling point
460.1 · 460.1±40.0 °C(Predicted)
Density
1.282 · 1.282±0.06 g/cm3(Predicted)
storage temp.
Hygroscopic, Refrigerator, under inert atmosphere
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid

Safety & regulation

Hazard information

Regulatory InformationChemical: 3-Pyridinemethanol, 4-(aminomethyl)-5-hydroxy-6-methyl-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

Regulatory information

Regulatory InformationChemical: 3-Pyridinemethanol, 4-(aminomethyl)-5-hydroxy-6-methyl-

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationA group of water-soluble vitamins, some of which are COENZYMES.
Tissue LocationsPlacenta；Prostate
Cellular LocationsExtracellular
Metabolite PathwaysHypophosphatasia；Vitamin B6 Metabolism

Applications

UsesPyridoxylamine is an advanced glycation end production (AGEs) and lipoxidation end products (ALEs) inhibitor, to protect against diabetes-induced retinal vascular lesions.

Upstream & downstream products

Suppliers48 total

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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+).

Related reactions

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