Cystamine

Not to be confused with cysteamine.

Cystamine
Names


IUPAC name 2,2'-Dithiobis(ethylamine)
Other names 2,2'-Dithiobisethanamine 2-Aminoethyl disulfide Decarboxycystine
Identifiers
CAS Number	51-85-4^Y
Abbreviations	AED
ChEBI	CHEBI:78757^N
ChEMBL	ChEMBL61350^Y
ChemSpider	2812^Y
Jmol interactive 3D	Image
PubChem	2915
UNII	R110LV8L02^Y
InChI InChI=1S/C4H12N2S2/c5-1-3-7-8-4-2-6/h1-6H2^Y Key: APQPRKLAWCIJEK-UHFFFAOYSA-N^Y InChI=1/C4H12N2S2/c5-1-3-7-8-4-2-6/h1-6H2 Key: APQPRKLAWCIJEK-UHFFFAOYAQ
SMILES S(SCCN)CCN
Properties
Chemical formula	C₄H₁₂N₂S₂
Molar mass	152.28 g/mol^[1]
Appearance	Viscous oil
Boiling point	Decomposes
Solubility in water	Miscible
Solubility in Ethanol	Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Cystamine is an organic disulfide. It is formed when cystine is heated, the result of decarboxylation. Cystamine is an unstable liquid and is generally handled as the dihydrochloride salt, C₄H₁₂N₂S₂·2HCl, which is stable to 203-214 °C at which point it decomposes. Cystamine is toxic if swallowed or inhaled and potentially harmful by contact.

Uses

Cystamine dihydrochloride is a useful reagent to derivatize various polymer monoliths for hydrophilic interaction liquid chromatography, as a crosslinking agent in the development of polymer hydrogels, and as a functional group in nanoparticles developed for siRNA and DNA delivery.

References

↑ Merck Index, 12th Edition, 2846.

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