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C8707

Sigma-Aldrich

Cystamine dihydrochloride

BioXtra

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:
12352200
PubChem Substance ID:
24893096
NACRES:
NA.25

product line

BioXtra

Assay

≥98% (TLC)

form

powder

impurities

≤0.0005% Phosphorus (P)
≤0.1% Insoluble matter

ign. residue

≤0.1%

mp

217-220 °C (dec.) (lit.)

solubility

H2O: 0.1 M, clear, colorless to light yellow

anion traces

sulfate (SO42-): ≤0.05%

cation traces

Al: ≤0.0005%
Ca: ≤0.02%
Cu: ≤0.0005%
Fe: ≤0.001%
K: ≤0.005%
Mg: ≤0.0005%
NH4+: ≤0.05%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

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 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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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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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
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
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
Zhongshan Liu et al.
Journal of chromatography. A, 1342, 70-77 (2014-04-15)
A polyhedral oligomeric silsesquioxane (POSS) hybrid monolith was simply prepared by using octaglycidyldimethylsilyl POSS (POSS-epoxy) and cystamine dihydrochloride as monomers via ring-opening polymerization. The effects of composition of prepolymerization solution and polycondensation temperature on the morphology and permeability of monolithic
Liang Gao et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(11), 3185-3192 (2012-02-22)
Autofluorescent microcapsules were assembled by covalent cross-linking of polysaccharide alginate dialdehyde (ADA) derivative and cystamine dihydrochloride (CM) through a layer-by-layer (LBL) technique. The formulated Schiff base and disulfide bonds render capsules with pH- and redox-responsive properties for pinpointed intracellular delivery
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