Aminopropionitrile

Aminopropionitrile
Structural formula of aminopropionitrile
Ball-and-stick model of the aminopropionitrile molecule
Names
Preferred IUPAC name
3-Aminopropanenitrile[1]
Other names
2-Cyanoethylamine[citation needed]
Identifiers
3D model (JSmol)
1698848
ChEBI
ChemSpider
ECHA InfoCard 100.005.261 Edit this at Wikidata
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).

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.

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 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. ^ Papadantonakis, Nikolaos; Matsuura, Shinobu; Ravid, Katya (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