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.
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| Names | |||
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| Preferred IUPAC name
3-Aminopropanenitrile[1] | |||
| Other names
2-Cyanoethylamine[citation needed]
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| Identifiers | |||
3D model (JSmol)
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| 3DMet | |||
| 1698848 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.005.261 | ||
| EC Number |
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| 600476 | |||
| KEGG | |||
| MeSH | Aminopropionitrile | ||
PubChem CID
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA)
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| 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
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Related compounds
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DBNPA | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biochemical and medical occurrence
editBAPN 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
editAminopropionitrile is prepared by the reaction of ammonia with acrylonitrile.[6]
See also
editReferences
edit- ^ "Aminopropionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Retrieved 7 June 2012.
- ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
- ^ "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.
- ^ 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.
- ^ 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
- ^ 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