Aminopropionitrile

Aminopropionitrile
Names
	Preferred IUPAC name 3-Aminopropanenitrile
	Other names 2-Cyanoethylamine[citation needed]
Identifiers
CAS Number	151-18-8 ;
3D model (JSmol)	Interactive image;
3DMet	B00834;
Beilstein Reference	1698848
ChEBI	CHEBI:27413 ;
ChemSpider	21241485 ;
ECHA InfoCard	100.005.261
EC Number	205-786-0;
Gmelin Reference	600476
KEGG	C05670 ;
MeSH	Aminopropionitrile
PubChem CID	1647;
RTECS number	UG0350000;
UNII	38D5LJ4KH2 ;
CompTox Dashboard (EPA)	DTXSID6048418 ;
	InChI InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2 Key: AGSPXMVUFBBBMO-UHFFFAOYSA-N ;
	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)
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.

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]

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

[PubChem_Compound-1] "Aminopropionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Retrieved 7 June 2012.

[CRC97-2] 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

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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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Biochemical and medical occurrence

Production

See also

References