Structure via PubChem · Public domain (PubChem)
cystamine
Sign in to saveAlso known as 2-Aminoethyl disulfide, beta-Mercaptoethylamine disulfide, Bis(beta-aminoethyl)disulfide, beta,beta'-Diaminodiethyl disulfide, Cysteinamine disulfide, 2,2'-Dithiobis(ethylamine), Decarboxycystine, Mercamine disulfide
Cystamine ('''2,2'-dithiobisethanamine''') 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.
In the Vinony graph
Vinony's link graph records 4 inbound references to cystamine, and connects out to deoxyribonucleic acid, International Standard Book Number and Alzheimer's disease.
Vinony files it under Aminoethyl compounds, Chembox image size set and ECHA InfoCard ID from Wikidata.
Vinony links it to 12 Wikipedia language editions.
Chemical data
- Formula
- C4H12N2S2
- Molecular weight
- 152.3 g/mol
- IUPAC name
- 2-(2-aminoethyldisulfanyl)ethanamine
- SMILES
- C(CSSCCN)N
- InChIKey
- APQPRKLAWCIJEK-UHFFFAOYSA-N
- XLogP
- -1
- Polar surface area
- 103 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,186 papers- Cystamine and cysteamine as inhibitors of transglutaminase activity in vivo.Bioscience reports · 2018
- Potential of cystamine and cysteamine in the treatment of neurodegenerative diseases.Progress in neuro-psychopharmacology & biological psychiatry · 2011
- Cysteamine/Cystamine Exert Anti-Mycobacterium abscessus Activity Alone or in Combination with Amikacin.International journal of molecular sciences · 2023
- Cystamine preparations exhibit anticoagulant activity.PloS one · 2015
- Cysteamine and cystamine.Methods in enzymology · 1987
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 152.044
Show 3 more facts
- chemical formula
- C₄H₁₂N₂S₂
- canonical SMILES
- C(CSSCCN)N
- Commons category
- Cystamine
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- Structure and synthesis
- Uses
- Interactions
- Toxicity
- Metabolism
- References
Cystamine ('''2,2'-dithiobisethanamine''') 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.
== Structure and synthesis == Cystamine is an organic disulfide which is formed when Cystine is heated as a result of decarboxylation. It is often used as sulfhydryl reagent, enzyme inhibitor and radiation-protective agent. Thiols can be synthesized to disulfides like cystamine through chemical oxidation with various oxidizing agents (molecular oxygen, metal ion, metal oxide, DMSO, nitric oxide, halogen and sodium perborate), through electrochemical oxidation and through borohydride exchange resin (BER)-transition metal salts systems (like BER-CuSo4).
Excerpted from Wikipedia’s “cystamine” article, available under the CC BY-SA 4.0 licence.