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CN

A3134

3-Aminopropionitrile fumarate salt

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

Key Documents

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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

Related Categories

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
GHS08

signalword

Danger

hcodes

H360FD

Hazard Classifications

Repr. 1B

Storage Class

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

wgk

WGK 3

ppe

Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000544080
0000544079
0000544080
0000544079
0000502374

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Transforming growth factor-beta2 induces expression of biologically active bone morphogenetic protein-1 in human trabecular meshwork cells
Tovar-Vidales T, et al.
Investigative Ophthalmology & Visual Science, 54(7), 4741-4748 (2013)
LMO1 synergizes with MYCN to promote neuroblastoma initiation and metastasis
Zhu Shizhen, et al.
Cancer Cell, 32(3), 310-323 (2017)
Force-driven evolution of mesoscale structure in engineered 3D microtissues and the modulation of tissue stiffening
Zhao R, et al.
Biomaterials, 35(19), 5056-5064 (2014)
George Sflomos et al.
EMBO molecular medicine, 13(3), e13180-e13180 (2021-02-23)
Invasive lobular carcinoma (ILC) is the most frequent special histological subtype of breast cancer, typically characterized by loss of E-cadherin. It has clinical features distinct from other estrogen receptor-positive (ER+ ) breast cancers but the molecular mechanisms underlying its characteristic
HIF2A--LOX Pathway Promotes Fibrotic Tissue Remodeling in Thyroid-Associated Orbitopathy
Hikage F, et al.
Endocrinology, 160(1) (2018)
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Global Trade Item Number

SKUGTIN
A3134-10G04061832945262
A3134-5G04061832945279
A3134-25G04061833360330

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