Aminopropionitrile
Chemical compound
From Wikipedia, the free encyclopedia
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 | |||
| Identifiers | |||
3D model (JSmol) |
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| 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 |
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
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]