Cystamine

Base Information

• Chemical Name: Cystamine
• CAS No.: 51-85-4
• Molecular Formula: C4H12 N2 S2
• Molecular Weight: 152.285
• Hs Code.: 2930909090
• European Community (EC) Number: 200-129-4
• UNII: R110LV8L02
• DSSTox Substance ID: DTXSID60199005
• Nikkaji Number: J4.128I
• Wikipedia: Cystamine
• Wikidata: Q2662688
• NCI Thesaurus Code: C97355
• Metabolomics Workbench ID: 71454
• ChEMBL ID: CHEMBL61350
• Mol file: 51-85-4.mol

Synonyms:2,2' Dithiobisethanamine;2,2'-Dithiobisethanamine;Calcium Salt, Cystamine;Cystamine;Cystamine Calcium Salt;Cystamine Diacetate;Cystamine Dihydrobromide;Cystamine Dihydrochloride;Cystamine Hydrobromide;Cystamine Hydrochloride;Cystamine Sulfate;Cystamine Sulfate (1:1);Cysteinamine Disulfide;Cystinamin;Cystineamine;Decarboxycystine;Diacetate, Cystamine;Diaminodiethyldisulfide;Dihydrobromide, Cystamine;Dihydrochloride, Cystamine;Disulfide, Cysteinamine;Hydrobromide, Cystamine;Hydrochloride, Cystamine;Sulfate, Cystamine

Chemical Property of Cystamine

Chemical Property:

• Melting Point: 135-136 °C
• Refractive Index: 1.5605 (estimate)
• Boiling Point: 106-108 °C(Press: 5 Torr)
• PKA: 8.97±0.10(Predicted)
• Flash Point: 114oC
• PSA: 102.64000
• Density: 1.090 (estimate)
• LogP: 1.68580
• Solubility.: Soluble in Water, DMSO, DMF, Methanol
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 152.04419074
• Heavy Atom Count: 8
• Complexity: 37

Purity/Quality:

99%, ^*data from raw suppliers

Aminoethyl-SS-ethylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C(CSSCCN)N
• Description: Aminoethyl-SS-ethylamine contains two primary amine terminal groups and a cleavable disulfide bond. The terminal amines can participate in chemical reactions with carboxylic acids, activated NHS esters and other carbonyl compounds. The disulfide bond can be cleaved by Dithiothreitol (DTT) reagent.

Technology Process of Cystamine

There total 30 articles about Cystamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Cysteamine (60-23-1) → 2,2'-dithio-bis[ethylamine] (51-85-4)

Guidance literature:

With polystyrene-bound diaryl selenoxide; In dichloromethane; for 1.5h;

DOI:10.1246/bcsj.59.879

Reference yield: 100.0%

S-nitroso-2-aminoethanethiol (67616-42-6) → 2,2'-dithio-bis[ethylamine] (51-85-4)

Guidance literature:

With Cu(II); for 24h;

DOI:10.1139/v2012-051

Reference yield: 90.0%

(Z)-1,4-Bis(2-aminoethyldithio)-2-butene dihydrochloride (111238-66-5) → 2,2'-dithio-bis[ethylamine] (51-85-4)

Guidance literature:

In water-d2; at 68 ℃; for 96h;

DOI:10.1021/je00051a023

upstream raw materials:

cysteine disulfide

L-cystine

2-aminoethylthiosulfonic acid

N,N'-(2,2'-disulfanediylbis(ethane-2,1-diyl))dibenzamide

Downstream raw materials:

D-pantethine

Cysteamine

bis[2-(3-phenyl-thioureido)ethyl]disulfide

Refernces

• 1、 Grachev, S. A.,Soroka, N. V.. "PRODUCTION OF THIYL RADICALS AND INVESTIGATION OF THEIR REACTIONS WITH OXYGEN AND 2-SULFOETHANETHIOSULFONIC ACID". . p. 1426 - 1432. Retrieved 1981.
• 2、 Katayama, Atsushi,Kamidate, Tamio,Watanabe, Hiroto. "Peroxidase-Catalyzed Chemiluminescence-Delay of Luminol for Determination of Traces of Copper(II)". . p. 2501 - 2504. Retrieved 1992.
• 3、 Morakinyo, Moshood K.,Chipinda, Itai,Hettick, Justin,Siegel, Paul D.,Abramson, Jonathan,Strongin, Robert,Martincigh, Bice S.,Simoyi, Reuben H.. "Detailed mechanistic investigation into the S-nitrosation of cysteamine". . p. 724 - 738. Retrieved 2012.
• 4、 Shanmugaprabha, Thangamariyappan,Selvakumar, Karuppaiah,Rajasekaran, Kasi,Sami, Ponnusamy. "A kinetic study of the oxidations of 2-mercaptoethanol and 2-mercaptoethylamine by heteropoly 11-tungsto-1- vanadophosphate in aqueous acidic medium". . p. 77 - 85. Retrieved 2016.
• 5、 Zhou, Li,Li, Tiejian,Sun, Ying,Tian, Hongwu,Gao, Cunxiu,Liu, Chunli,Kong, Lingli,Zhang, Guimin,Shi, Tiesheng. "Mechanistic scrutiny of the oxidations of thiol-containing drugs cysteamine and d-penicillamine by cis-diamminetetrachloroplatinum(IV)". supporting information. p. 548 - 557. Retrieved 2020/12/18.
• 6、 Stoffel, Jonathan T.,Riordan, Kimberly T.,Tsui, Emily Y.. "Accelerated reduction and solubilization of elemental sulfur by 1,2-aminothiols". supporting information. p. 12488 - 12491. Retrieved 2021/12/04.