Aminopropionitrile, also known as β-aminopropionitrile (BAPN), is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with both
amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
and
nitrile functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...
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 suita ...
. 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." It can cause
osteolathyrism
Osteolathyrism, sometimes referred to as odoratism, is a form of the disease Lathyrism. The disease results from the ingestion of '' Lathyrus odoratus'' seeds (sweet peas). The toxin found in the sweet peas is ( beta-aminopropionitrile), which a ...
,
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'', ''ke ...
, and/or
angiolathyrism
Angiolathyrism is a form of Lathyrism disease. It is mainly caused the consumption of '' Lathyrus sativus'' (also known as ''grass pea'') and to a lesser degree by ''Lathyrus cicera'', '' Lathyrus ochrus'' and ''Lathyrus clymenum''antirheumatic
Disease-modifying antirheumatic drugs (DMARDs) comprise a category of otherwise unrelated disease-modifying drugs defined by their use in rheumatoid arthritis to slow down disease progression. The term is often used in contrast to nonsteroidal ...
agent in veterinary medicine.
It has attracted interest as an
anticancer agent
Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemotherap ...
.
Production
Aminopropionitrile is prepared by the reaction of
ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...
with
acrylonitrile
Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecula ...
.
[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 molecules into highly reactive aldehydes that form cross-links in extracellular matr ...
*
Marfan syndrome
References
{{Anti-inflammatory products
Amines
Nitriles