Aminopropionitrile

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Aminopropionitrile
Structural formula of aminopropionitrile
Ball-and-stick model of the aminopropionitrile molecule
Names
IUPAC name
3-Aminopropanenitrile[1]
Other names
2-Cyanoethylamine[citation needed]
Identifiers
151-18-8 YesY
3DMet B00834
ATCvet code QM01AX91
1698848
ChEBI CHEBI:27413 YesY
ChemSpider 21241485 YesY
EC number 205-786-0
600476
Jmol-3D images Image
KEGG C05670 YesY
MeSH Aminopropionitrile
PubChem 1647
RTECS number UG0350000
UNII 38D5LJ4KH2 YesY
Properties
C3H6N2
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
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

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[edit]

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]

Production[edit]

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

See also[edit]

References[edit]

  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, and 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 3433087. 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