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| Names | |||
|---|---|---|---|
| Preferred IUPAC name 3-Aminopropanenitrile | |||
| Other names 2-Cyanoethylamine | |||
| Identifiers | |||
| CAS Number | |||
| 3D model (JSmol) | |||
| Beilstein Reference | 1698848 | ||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.005.261 
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| EC Number |
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| Gmelin Reference | 600476 | ||
| KEGG | |||
| MeSH | Aminopropionitrile | ||
| PubChem CID | |||
| RTECS number |
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| UNII | |||
| CompTox Dashboard (EPA) | |||
InChI
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SMILES
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| Properties | |||
| Chemical formula | C3H6N2 | ||
| Molar mass | 70.095 g·mol | ||
| 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) | ||
| Pharmacology | |||
| ATCvet code | QM01AX91 (WHO) | ||
| Related compounds | |||
| Related alkanenitriles | |||
| Related compounds | DBNPA | ||
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 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''. 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." It can cause osteolathyrism, neurolathyrism, and/or angiolathyrism.
It is an antirheumatic agent in veterinary medicine.
It has attracted interest as an anticancer agent.
Production
Aminopropionitrile is prepared by the reaction of ammonia with acrylonitrile.
See also
References
- "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
| Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA) | |
|---|---|
| pyrazolones / pyrazolidines | |
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
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| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
| Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use. | |
