Binary ethylenimine (BEI) is a preparation of

aziridine Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its deriva ...

. It can be produced by heating bromoethylamine hydrobromide or 2-aminoethyl hydrogen sulfate in the presence of

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

( Gabriel method). It contains at least one three-membered ring which is very reactive because of the ring strain. It is used to inactivate the

foot-and-mouth disease Foot-and-mouth disease (FMD) or hoof-and-mouth disease (HMD) is an infectious disease, infectious and sometimes fatal virus (biology), viral disease that primarily affects even-toed ungulates, including domestic and wild Bovidae, bovids. The vir ...

virus in

vaccine A vaccine is a biological Dosage form, preparation that provides active acquired immunity to a particular infectious disease, infectious or cancer, malignant disease. The safety and effectiveness of vaccines has been widely studied and verifi ...

s for

cattle Cattle (''Bos taurus'') are large, domesticated, bovid ungulates widely kept as livestock. They are prominent modern members of the subfamily Bovinae and the most widespread species of the genus '' Bos''. Mature female cattle are calle ...

, as well as other viruses and

mycoplasma ''Mycoplasma'' is a genus of bacteria that, like the other members of the class ''Mollicutes'', lack a cell wall, and its peptidoglycan, around their cell membrane. The absence of peptidoglycan makes them naturally resistant to antibiotics ...

blood Blood is a body fluid in the circulatory system of humans and other vertebrates that delivers necessary substances such as nutrients and oxygen to the cells, and transports metabolic waste products away from those same cells. Blood is com ...

samples. Contrary to early assumptions that ethylenimines only modified

nucleic acid Nucleic acids are large biomolecules that are crucial in all cells and viruses. They are composed of nucleotides, which are the monomer components: a pentose, 5-carbon sugar, a phosphate group and a nitrogenous base. The two main classes of nuclei ...

s, it was found that trimeric ethylenimine also alters

proteins Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, re ...

in virus preparations, especially at higher pH values. The modification of the proteins affected viral particle uptake into cells. This should be taken into consideration when using BEI and other ethyleneimines as well.

Safety

BEI is very hazardous since it attacks nucleic acids and proteins as described above. It can be neutralised by

sodium thiosulfate Sodium thiosulfate (sodium thiosulphate) is an inorganic compound with the formula . Typically it is available as the white or colorless pentahydrate (x = 5), which is a white solid that dissolves well in water. The compound is a reducing agent an ...

; the thiosulfate is a nucleophile which opens the three-membered ring. The presence of BEI can be tested for using

silver nitrate Silver nitrate is an inorganic compound with chemical formula . It is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides. It was once called ''lunar causti ...

solution.

Safety

References

Further reading