Structural formula of aminopropionitrile
Ball-and-stick model of the aminopropionitrile molecule
IUPAC name
Other names
151-18-8 YesY
3D model (Jmol) Interactive image
3DMet B00834
ChEBI CHEBI:27413 YesY
ChemSpider 21241485 YesY
ECHA InfoCard 100.005.261
EC Number 205-786-0
KEGG C05670 YesY
MeSH Aminopropionitrile
PubChem 1647
RTECS number UG0350000
Molar mass 70.10 g·mol−1
Appearance Colourless liquid
Boiling point 79 to 81 °C; 174 to 178 °F; 352 to 354 K at 2.1 kPa
QM01AX91 (WHO)
Related compounds
Related alkanenitriles
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[2] 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."[3] It can cause osteolathyrism, neurolathyrism, and/or angiolathyrism.

It is an antirheumatic agent in veterinary medicine.

It has attracted interest as an anticancer agent.[4]


Aminopropionitrile is prepared by the reaction of ammonia with acrylonitrile.[5]

See also


  1. "Aminopropionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Retrieved 7 June 2012.
  2. "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.
  3. Nikolaos Papadantonakis; Shinobu Matsuura; Katya Ravid. "Megakaryocyte pathology and bone marrow fibrosis: the lysyl oxidase connection". Blood. 120 (9): 1774–1781. doi:10.1182/blood-2012-02-402594. PMC 3433087Freely accessible. PMID 22767499.
  4. 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
  5. 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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