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A3134

3-Aminopropionitrile fumarate salt

Name: 3-Aminopropionitrile fumarate salt
Brand: SIGMA

synthetic (organic), ≥98% (TLC), irreversible inhibitor of lysyl oxidase, powder

Synonym(s):

β-Alaninenitrile

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About This Item

Linear Formula:

NH₂CH₂CH₂CN · ½ (HO₂CCH=CHCO₂H)

CAS Number:

2079-89-2

Molecular Weight:

128.13

MDL number:

MFCD00013142

UNSPSC Code:

12352202

PubChem Substance ID:

24278224

NACRES:

NA.77

EC Number:

218-208-7

Beilstein/REAXYS Number:

3573532

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Properties

Product Name

3-Aminopropionitrile fumarate salt, metabolite

biological source

synthetic (organic)

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

177 °C (dec.) (lit.)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

SMILES string

NCCC#N.NCCC#N.OC(=O)\C=C\C(O)=O

InChI

1S/C4H4O4.2C3H6N2/c5-3(6)1-2-4(7)8;2*4-2-1-3-5/h1-2H,(H,5,6)(H,7,8);2*1-2,4H2/b2-1+;;

InChI key

NYMXYZMHOZAPHQ-SEPHDYHBSA-N

Description

Application

3-Aminopropionitrile fumarate salt has been used as a lysyl oxidase (LOX) inhibitor:

to inhibit collagen cross-linking during microtissue formation and culture
in LIM domain only 1 (LMO1)- or vector-expressing BE2C neuroblastoma cell line in transwell migration and invasion assay
in lysyl oxidase (LOX) activity assay
to study requirement of LOX activity for inducing hypoxia-inducible factor (HIF)2A-dependent stiffness in mouse organoids

Biochem/physiol Actions

3-Aminopropionitrile (β-Aminopropionitrile (BAPN)) functions as an irreversible inhibitor of lysyl oxidase (LOX), an enzyme involved in collagen cross-linking.

In mammals, metabolism of 3-aminopropionitrile leads to release of cyanide ions. Metabolic activity is localized in the microsomal fraction of the liver, and is believed to proceed through a free-radical pathway.