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Details

Stereochemistry ACHIRAL
Molecular Formula C3H6N2
Molecular Weight 70.0931
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-AMINOPROPANENITRILE

SMILES

NCCC#N

InChI

InChIKey=AGSPXMVUFBBBMO-UHFFFAOYSA-N
InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2

HIDE SMILES / InChI

Description

3-Aminopropionitrile (beta-aminopropionitrile, BAPN) is a poisonous substance found in Lathyrus spp. (wild peas), for example, Lathyrus hirsutus (wild winter pea), sometimes sown with grasses to provide early-spring grazing. BAPN is a specific and irreversible inhibitor of LOX activity. It has been shown to reduce body weight gain and improve the metabolic profile in diet-induced obesity in rats. The administration of beta-aminopropionitrile has been proposed for pharmacological control of unwanted scar tissue in human beings. BAPN has been shown to have preventive effect in the development of fibrosis by decreasing tissue damage in an experimental model of corrosive esophagitis in rats. BAPN is FDA approved for the treatment of tendinitis of the superficial digital flexor tendon (SDFT) in horses where there is sonographic evidence of fiber tearing.

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
For treatment of tendinitis of the superficial digital flexor tendon (SDFT) in horses where there is sonographic evidence of fiber tearing. Administer 7 mg by intralesional injection every other day for five treatments beginning about 30 days after initial injury.
Route of Administration: Other
In Vitro Use Guide
The initial interaction of BAPN with aortic lysyl oxidase is competitive with elastin or alkyl amine substrates. Irreversible inhibition develops in a time- and temperature-dependent fashion upon incubation of enzyme with BAPN in the absence of substrate with a limiting inactivation rate constant of 0.16 min-1 and a KI of 6 uM at 37 degrees C.