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Aminopropionitrile








Aminopropionitrile


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Aminopropionitrile




Structural formula of aminopropionitrile


Ball-and-stick model of the aminopropionitrile molecule

Names

IUPAC name
3-Aminopropanenitrile[1]

Other names
2-Cyanoethylamine[citation needed]

Identifiers

CAS Number



  • 151-18-8 ☑Y


3D model (JSmol)


  • Interactive image

3DMet

B00834

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





Properties

Chemical formula


C3H6N2

Molar mass
70.10 g·mol−1
Appearance
Colourless liquid

Boiling point
 79 to 81 °C; 174 to 178 °F; 352 to 354 K at 2.1 kPa
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


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.




Contents





  • 1 Biochemical and medical occurrence


  • 2 Production


  • 3 See also


  • 4 References




Biochemical and medical occurrence[edit]


BAPN is the toxic constituent of peas from Lathyrus plants, e.g., lathyrus odoratus.[2] 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."[3] It can cause osteolathyrism, neurolathyrism, and/or angiolathyrism.


It is an antirheumatic agent in veterinary medicine.


It has attracted interest as an anticancer agent.[4]



Production[edit]


Aminopropionitrile is prepared by the reaction of ammonia with acrylonitrile.[5]



See also[edit]


  • Kashin-Beck disease

  • Lysyl oxidase

  • Marfan syndrome


References[edit]




  1. ^ "Aminopropionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Retrieved 7 June 2012..mw-parser-output cite.citationfont-style:inherit.mw-parser-output qquotes:"""""""'""'".mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em


  2. ^ "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.


  3. ^ Nikolaos Papadantonakis; Shinobu Matsuura; Katya Ravid. "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.


  4. ^ 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


  5. ^ 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















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