Aminopropionitrile, also known as β-aminopropionitrile (BAPN), is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with both
amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
and
nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...
functional group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
s. 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
The sweet pea, ''Lathyrus odoratus'', is a flowering plant in the genus ''Lathyrus'' in the family Fabaceae (legumes), native to Sicily, southern Italy and the Aegean Islands.
It is an annual climbing plant, growing to a height of , where suit ...
''. 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
Neurolathyrism, is a neurological disease of humans, caused by eating certain legumes of the genus ''Lathyrus''. This disease is mainly associated with the consumption of ''Lathyrus sativus'' (also known as ''grass pea'', ''chickling pea'', ''kes ...
, 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
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
with
acrylonitrile
Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group () linked to a nitrile (). It is an im ...
.
[Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2005. ]
See also
*
Kashin-Beck disease
*
Lysyl oxidase
Lysyl oxidase (LOX), also known as protein-lysine 6-oxidase, is an enzyme that, in humans, is encoded by the ''LOX'' gene. It catalyzes the conversion of lysine residues into its aldehyde derivative allysine. Allysine form cross-links in extr ...
*
Marfan syndrome
Marfan syndrome (MFS) is a multi-systemic genetic disorder that affects the connective tissue. Those with the condition tend to be tall and thin, with dolichostenomelia, long arms, legs, Arachnodactyly, fingers, and toes. They also typically ha ...
References
{{Anti-inflammatory products
Amines
Nitriles
Plant toxins