Aminopropionitrile

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.

Aminopropionitrile

Names
Preferred IUPAC name 3-Aminopropanenitrile[1]
Other names 2-Cyanoethylamine[citation needed]
Identifiers
CAS Number	151-18-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1698848
ChEBI	CHEBI:27413 Y
ChemSpider	21241485 Y
ECHA InfoCard	100.005.261
EC Number	205-786-0
Gmelin Reference	600476
KEGG	C05670 Y
MeSH	Aminopropionitrile
PubChem CID	1647
RTECS number	UG0350000
UNII	38D5LJ4KH2 Y
CompTox Dashboard (EPA)	DTXSID6048418
InChI InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2 Y Key: AGSPXMVUFBBBMO-UHFFFAOYSA-N Y
SMILES 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
ATCvet code	QM01AX91 (WHO)
Related compounds
Related alkanenitriles	Acetonitrile Aminoacetonitrile Glycolonitrile Cyanogen Propanenitrile Malononitrile Pivalonitrile Acetone cyanohydrin Butyronitrile Succinonitrile Tetramethylsuccinonitrile
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

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]

See also

• Kashin-Beck disease
• Lysyl oxidase
• Marfan syndrome

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. 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.
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