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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

Quality Level

200

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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Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

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)

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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
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
Yasue Ishii-Osai et al.
Journal of dermatological science, 67(1), 51-60 (2012-05-25)
N-propionyl-4-S-cysteaminylphenol (NPr-4-S-CAP) is selectively incorporated into melanoma cells and degrades them. However, it remains unclear whether NPr-4-S-CAP can induce cell death associated with the induction of host immune responses and tumor suppression in vivo. To examine the molecular mechanism of
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