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A3134 Sigma-Aldrich

3-Aminopropionitrile fumarate salt

metabolite

Synonym: β-Alaninenitrile

  • CAS Number 2079-89-2

  • Linear Formula NH2CH2CH2CN · ½ (HO2CCH=CHCO2H)

  • Molecular Weight 128.13

  •  Beilstein/REAXYS Number 3573532

  •  EC Number 218-208-7

  •  PubChem Substance ID 24278224

  •  NACRES NA.77

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Properties

Related Categories Biochemicals and Reagents, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, L to O,
Quality Level   200
biological source   synthetic (organic)
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

Packaging

5, 10, 25 g in poly bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

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Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
UG0700000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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