Cystamine

Cystamine
IUPAC name 2,2'-Dithiobis(ethylamine)
Other names 2,2'-Dithiobisethanamine 2-Aminoethyl disulfide Decarboxycystine
Identifiers
Abbreviations	AED
CAS number	51-85-4 Y
PubChem	2915
ChemSpider	2812 Y
UNII	R110LV8L02 Y
ChEMBL	CHEMBL61350 Y
Jmol-3D images	Image 1
SMILES S(SCCN)CCN
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
Properties
Molecular formula	C4H12N2S2
Molar mass	152.28 g/mol[1]
Appearance	Viscous oil
Boiling point	Decomposes
Solubility in water	Miscible
Solubility in Ethanol	Soluble
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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