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A3134

Sigma-Aldrich

3-Aminopropionitrile fumarate salt

metabolite

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Synonym(s):
β-Alaninenitrile
Linear Formula:
NH2CH2CH2CN · ½ (HO2CCH=CHCO2H)
CAS Number:
Molecular Weight:
128.13
Beilstein:
3573532
EC Number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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

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1 of 4

This Item
C9375B2515M4002
5-Carboxy-2-thiouracil

Sigma-Aldrich

C9375

5-Carboxy-2-thiouracil

assay

≥98% (TLC)

assay

≥98% (TLC)

assay

≥97% (TLC)

assay

≥99% (HPLC)

form

powder

form

powder

form

powder

form

powder

mp

177 °C (dec.) (lit.)

mp

-

mp

224-226  °C

mp

-

solubility

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

solubility

1 M NaOH: 50 mg/mL, clear, colorless to faintly yellow

solubility

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

solubility

methanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

A3134-25G:4.548173185262E12
A3134-5G:4.548173185279E12
A3134-10G:4.548173185255E12


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