Cystamine (HCID 2915)

Overview

Cystamine is an organic disulfide obtgained by oxidative dimerisation of cysteamine. It has a role as an EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor. It is an organic disulfide and a primary amino compound. It is functionally related to a cysteamine.

Names & identifiers

Preferred name: Cystamine
IUPAC: 2-(2-aminoethyldisulfanyl)ethanamine
English name: 2,2'-dithiobis(ethylamine)
Molecular formula: C4H12N2S2
Molecular weight: 152.28

Names & synonyms

cystamine51-85-4Decarboxycystine2,2'-Dithiobis(ethylamine)CystineamineCystinaminMercamine disulfideCysteinamine disulfideEthanamine, 2,2'-dithiobis-Becaptan disulfureBis(beta-aminoethyl)disulfide2,2'-Dithiobisethanamine

Show more names

2,2'-disulfanediyldiethanamineL-1591Cystinamine2,2'-Dithiodiethylamine2,2-DIAMINODIETHYLDISULPHIDE

beta-Mercaptoethylamine disulfidebeta,beta'-Diaminodiethyl disulfide1591 LR110LV8L02CHEBI:78757DTXSID601990052-(2-aminoethyldisulfanyl)ethylamine2,2'-Dithiobis[ethylamine]

Database identifiers

CAS: 51-85-4
PubChem CID: 2915
DTXSID: DTXSID60199005
ChEMBL: CHEMBL61350
ChEBI: CHEBI:78757
UNII: R110LV8L02
EC Number: 200-129-4
Nikkaji: J4.128I

Properties

Computed structural properties

XLogP: -1
Topological polar surface area: 103 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 5
Heavy atoms: 8
Formal charge: 0
Complexity: 37

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Sulfur Compounds

Physical DescriptionViscous liquid; [Merck Index]

Physicochemical properties

Melting point: 135 · 135-136 °C
Boiling point: 106 · 106-108 °C(Press: 5 Torr)
Density: 1.09 · 1.090 (estimate)
refractive index: 1.5605 · 1.5605 (estimate)
storage temp.: -20 °C · Storage temp. -20°C
solubility: Soluble in Water, DMSO, DMF, Methanol
pka: 8.97 · 8.97±0.10(Predicted)
form: Liquid
color: Light yellow to brown
FDA UNII: 110 LV8L02 · R110LV8L02
Symbol(GHS): 5 · GHS05,GHS07
Signal word: Danger
Hazard statements: 315 · H315-H318-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501

Safety & regulation

Hazard information

Hazards SummaryCauses general anesthesia, elevated blood pressure, convulsions, and lung changes in subcutaneous lethal-dose studies of mammals; [RTECS] See Cystamine dihydrochloride.

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Safety data

Signal word: Danger
Symbol(GHS): GHS05,GHS07
Hazard statements: H315-H318-H335
Precautionary statements: P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 3 items

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military.

Chemical agents that react with SH groups. This is a chemically diverse group that is used for a variety of purposes. Among these are enzyme inhibition, enzyme reactivation or protection, and labelling.

Uses & manufacturing

UsesA radiation-protective agent that interferes with sulfhydryl enzymes. It may also protect against carbon tetrachloride liver damage. [ChemIDplus]

Applications · 2 items

DescriptionAminoethyl-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.

UsesCystamine is the disulfide form of the free thiol, cysteamine. Cystamine is an orally active transglutaminase (Tgase) inhibitor. Cystamine also has inhibition activity for caspase-3 with an IC50 value of 23.6 μM. Cystamine can be used for the research of severals diseases including Huntington's disease (HD) [1][2][3].