Aminopropionitrile

Aminopropionitrile
Structural formula of aminopropionitrile
Ball-and-stick model of the aminopropionitrile molecule
Names
Preferred IUPAC name
3-Aminopropanenitrile[1]
Other names
2-Cyanoethylamine[citation needed]
Identifiers
CAS Number
  • 151-18-8 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00834
Beilstein Reference
 1698848
ChEBI
  • CHEBI:27413 checkY
ChemSpider
  • 21241485 checkY
ECHA InfoCard 100.005.261 Edit this at Wikidata
EC Number
  • 205-786-0
Gmelin Reference
 600476
KEGG
  • C05670 checkY
MeSH Aminopropionitrile
PubChem CID
  • 1647
RTECS number
  • UG0350000
UNII
  • 38D5LJ4KH2 checkY
CompTox Dashboard (EPA)
  • DTXSID6048418 Edit this at Wikidata
InChI
  • InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2 checkY
    Key: AGSPXMVUFBBBMO-UHFFFAOYSA-N checkY
  • NCCC#N
Properties
Chemical formula
 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
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
Chemical compound

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.[3] 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."[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]

See also

References

  1. ^ "Aminopropionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Retrieved 7 June 2012.
  2. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
  3. ^ "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.
  4. ^ Nikolaos Papadantonakis; Shinobu Matsuura; Katya Ravid (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.
  5. ^ 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
  6. ^ 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
  • v
  • t
  • e
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidinessalicylatesacetic acid derivatives
and related substancesoxicamspropionic acid
derivatives (profens)n-arylanthranilic
acids (fenamates)COX-2 inhibitors
(coxibs)otherNSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; †withdrawn drugs; ‡veterinary use.
  • category
  • commons
  • portal