Aminopropionitrile Explained

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.^[1] 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."^[2] It can cause osteolathyrism, neurolathyrism, and/or angiolathyrism.

It is an antirheumatic agent in veterinary medicine.

It has attracted interest as an anticancer agent.^[3]

Production

Aminopropionitrile is prepared by the reaction of ammonia with acrylonitrile.^[4]

See also

• Kashin-Beck disease
• Lysyl oxidase
• Marfan syndrome

Notes and References

1. Web site: Lathyrus. 2014. American Association for Clinical Chemistry. 15 October 2014. Washington, DC. 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..
2. Megakaryocyte pathology and bone marrow fibrosis: the lysyl oxidase connection. Blood. 120. 9. 1774–1781. Nikolaos Papadantonakis . Shinobu Matsuura . Katya Ravid . 2012. 10.1182/blood-2012-02-402594. 3433087. 22767499.
3. Chvapil, Milos "Inhibition of breast adenocarcinoma growth by intratumoral injection of lipophilic long-acting lathyrogens" Anti-Cancer Drugs 2005, volume 16, 201-210.
4. Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.