Skip to Content
Merck
All Photos(4)

Key Documents

View All Documentation

A3134

Sigma-Aldrich

3-Aminopropionitrile fumarate salt

metabolite

Synonym(s):

β-Alaninenitrile

Sign Into View Organizational & Contract Pricing
All Photos(4)

About This Item

Linear Formula:
NH2CH2CH2CN · ½ (HO2CCH=CHCO2H)
CAS Number:
2079-89-2
Molecular Weight:
128.13
Beilstein:
3573532
EC Number:
218-208-7
UNSPSC Code:
12352202
PubChem Substance ID:
24278224
NACRES:
NA.77

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Danger

Hazard Statements

H360FD

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Shota Tomida et al.
Scientific reports, 9(1), 10751-10751 (2019-07-26)
Aortic dissection is a life-threatening condition, which is characterised by separation of the constituent layers of the aortic wall. We have recently shown that monocyte/macrophage infiltration into the aortic wall is a pathogenic mechanism of the condition. In the present
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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service