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C121509

Sigma-Aldrich

Cystamine dihydrochloride

96%

Synonym(s):

2,2′-Diaminodiethyl disulfide dihydrochloride, 2,2′-Dithiobis(ethylamine) dihydrochloride, Decarboxycystine dihydrochloride

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About This Item

Linear Formula:
NH2CH2CH2SSCH2CH2NH2 · 2HCl
CAS Number:
56-17-7
Molecular Weight:
225.20
Beilstein:
3616850
EC Number:
200-260-7
MDL number:
MFCD00012905
UNSPSC Code:
12352100
PubChem Substance ID:
24892384
NACRES:
NA.22

Assay

96%

form

powder

mp

217-220 °C (dec.) (lit.)

SMILES string

Cl[H].Cl[H].NCCSSCCN

InChI

1S/C4H12N2S2.2ClH/c5-1-3-7-8-4-2-6;;/h1-6H2;2*1H

InChI key

YUFRRMZSSPQMOS-UHFFFAOYSA-N

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Application

Cystamine dihydrochloride can be utilized as a building block in the synthesis of disulfide cross-linked oligodeoxyribonucleotides and psammaplin A . It can be also used to functionalize PGMA (poly(glycidyl methacrylate) microsphere) by introducing sulfhydryl groups for the further fabrication of silver nanoparticles (AgNPs).
Heparin antagonist and sulfhydryl modifying reagent

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and characterization of disulfide cross-linked oligonucleotides
Ferentz A E, et al.
Journal of the American Chemical Society, 115(20), 9006-9014 (1993)
In situ synthesis of monodisperse silver nanoparticles on sulfhydryl-functionalized poly (glycidyl methacrylate) microspheres for catalytic reduction of 4-nitrophenol
Zhang W, et al.
Industrial & Engineering Chemistry Research, 54(25), 6480-6488 (2015)
Qianjiao Yang et al.
Molecules (Basel, Switzerland), 15(12), 8784-8795 (2010-12-04)
Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland's reagent reduction as key step. The longest linear
Thorsten Overath et al.
Molecular & cellular proteomics : MCP, 11(8), 467-477 (2012-05-05)
The post-translational modification of proteins with O-GlcNAc is involved in various cellular processes including signal transduction, transcription, translation, and nuclear transport. This transient protein modification enables cells or tissues to adapt to nutrient conditions or stress. O-Glycosylation of the 26
Shosuke Ito et al.
Biochemical pharmacology, 84(5), 646-653 (2012-06-26)
Metastatic melanoma is resistant to conventional therapies. N-propionyl-4-S-cysteaminylphenol (NPrCAP), an N-protected sulfur-amine analog of tyrosine, is a good substrate for tyrosinase and is selectively incorporated into melanoma cells, causing cytotoxicity in vitro and in vivo. We have recently shown that
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