Aminopropionitrile

Aminopropionitrile, also known as β-aminopropionitrile (BAPN), is an organic compound with both amine and nitrile functional groups. It is a colourless liquid. The compound occurs naturally and is of interest in the biomedical community.

Aminopropionitrile
Structural formula of aminopropionitrile
Ball-and-stick model of the aminopropionitrile molecule
Names
Preferred IUPAC name
3-Aminopropanenitrile[1]
Other names
2-Cyanoethylamine
Identifiers
3D model (JSmol)
3DMet
1698848
ChEBI
ChemSpider
ECHA InfoCard 100.005.261
EC Number
  • 205-786-0
600476
KEGG
MeSH Aminopropionitrile
RTECS number
  • UG0350000
UNII
  • InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2 checkY
    Key: AGSPXMVUFBBBMO-UHFFFAOYSA-N checkY
  • NCCC#N
Properties
C3H6N2
Molar mass 70.095 g·mol−1
Appearance Colourless liquid
Boiling point 79 to 81 °C; 174 to 178 °F; 352 to 354 K at 2.1 kPa
Acidity (pKa) 7.80 (conjugate acid; 20 °C, H2O)[2]
Pharmacology
QM01AX91 (WHO)
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Biochemical and medical occurrence

BAPN is the toxic constituent of peas from Lathyrus plants, e.g., lathyrus odoratus.[3] Lathyrism, a disease known for centuries, encompasses 2 distinct entities: a disorder of the nervous system (neurolathyrism) leading to limb paralysis, and a disorder of connective tissue, causing either bone deformity (osteolathyrism) or aortic aneurisms (angiolathyrim). BAPN causes osteolathyrism and angiolathyrism when ingested in large quantities."[4] It can cause osteolathyrism, neurolathyrism, and/or angiolathyrism.

It is an antirheumatic agent in veterinary medicine.

It has attracted interest as an anticancer agent.[5]

Production

Aminopropionitrile is prepared by the reaction of ammonia with acrylonitrile.[6]

See also

References
  1. "Aminopropionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Retrieved 7 June 2012.
  2. Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
  3. "Lathyrus". Washington, DC: American Association for Clinical Chemistry. 2014. Retrieved 15 October 2014. Beta-amino-propionitrile (BAPN) found in lathyrus odoratus (common garden sweet pea) is thought to be responsible for osteolathyrism, which in humans is poorly documented.
  4. Nikolaos Papadantonakis; Shinobu Matsuura; Katya Ravid (2012). "Megakaryocyte pathology and bone marrow fibrosis: the lysyl oxidase connection". Blood. 120 (9): 1774–1781. doi:10.1182/blood-2012-02-402594. PMC 3433087. PMID 22767499.
  5. Chvapil, Milos "Inhibition of breast adenocarcinoma growth by intratumoral injection of lipophilic long-acting lathyrogens" Anti-Cancer Drugs 2005, volume 16, 201-210. doi:10.1097/00001813-200502000-00013
  6. Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
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