Name: 2,2'-Dithiobis(ethylamine)
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Price

Stock

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$--

In stock

Solubility

In DMSO: 100 mg/mL (656.69 mM; Need ultrasonic)

Storage

Pure form, -20°C, 3 years; In solvent, -80°C, 6 months; -20°C, 1 month

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

2-(2-aminoethyldisulfanyl)ethanamine

InChI Key

APQPRKLAWCIJEK-UHFFFAOYSA-N

InChI

InChI=1S/C4H12N2S2/c5-1-3-7-8-4-2-6/h1-6H2

SMILES

C(CSSCCN)N

1. Cystamine and cysteamine as inhibitors of transglutaminase activity in vivo

Thomas M Jeitner, John T Pinto, Arthur J L Cooper Biosci Rep. 2018 Sep 5;38(5):BSR20180691.doi: 10.1042/BSR20180691.Print 2018 Oct 31.

Cystamine is commonly used as a transglutaminase inhibitor. This disulphide undergoes reduction in vivo to the aminothiol compound, cysteamine. Thus, the mechanism by which cystamine inhibits transglutaminase activity in vivo could be due to either cystamine or cysteamine, which depends on the local redox environment. Cystamine inactivates transglutaminases by promoting the oxidation of two vicinal cysteine residues on the enzyme to an allosteric disulphide, whereas cysteamine acts as a competitive inhibitor for transamidation reactions catalyzed by this enzyme. The latter mechanism is likely to result in the formation of a unique biomarker, N-(γ-glutamyl)cysteamine that could serve to indicate how cyst(e)amine acts to inhibit transglutaminases inside cells and the body.

2. Potential of cystamine and cysteamine in the treatment of neurodegenerative diseases

C Gibrat, F Cicchetti Prog Neuropsychopharmacol Biol Psychiatry. 2011 Mar 30;35(2):380-9.doi: 10.1016/j.pnpbp.2010.11.023.Epub 2010 Nov 24.

Neurodegenerative disorders are a subset of disabling pathologies characterized, in part, by a progressive and specific loss of certain brain cell populations. Current therapeutic approaches for the treatment of these disorders are mainly designed towards symptom management and do not manifestly block their typified neuronal loss. However, research conducted over the past decade has reflected the increasing interest and need to find disease-modifying molecules. Among the several neuroprotective agents emerging from experimental animal work, cystamine, as well as its reduced form cysteamine, have been identified as potential candidate drugs. Given the significant benefits observed in a Huntington's disease (HD) model, cysteamine has recently leaped to clinical trial. Here, we review the beneficial properties of these compounds as reported in animal studies, their mechanistic underpinnings, and their potential implications for the future treatment of patients suffering from neurodegenerative diseases, and more specifically for HD and Parkinson's disease (PD).

3. Three salts from the reactions of cysteamine and cystamine with L-(+)-tartaric acid

Amina Benylles, Donald Cairns, Philip J Cox, Graeme Kay Acta Crystallogr C. 2013 Jun;69(Pt 6):658-64.doi: 10.1107/S0108270113012377.Epub 2013 May 17.

Reaction between cysteamine (systematic name: 2-aminoethanethiol, C2H7NS) and L-(+)-tartaric acid [systematic name: (2R,3R)-2,3-dihydroxybutanedioic acid, C4H6O6] results in a mixture of cysteamine tartrate(1-) monohydrate, C2H8NS(+)·C4H5O6(-)·H2O, (I), and cystamine bis[tartrate(1-)] dihydrate, C4H14N2S2(2+)·2C4H5O6(-)·2H2O, (III). Cystamine [systematic name: 2,2'-dithiobis(ethylamine), C4H12N2S2], reacts with L-(+)-tartaric acid to produce a mixture of cystamine tartrate(2-), C4H14N2S2(2+)·C4H4O6(2-), (II), and (III). In each crystal structure, the anions are linked by O-H···O hydrogen bonds that run parallel to the a axis. In addition, hydrogen bonding involving protonated amino groups in all three salts, and water molecules in (I) and (III), leads to extensive three-dimensional hydrogen-bonding networks. All three salts crystallize in the orthorhombic space group P2(1)2(1)2(1).

ConcentrationVolumeMass	1 mg	5 mg	10 mg
1 mM	6.5669 mL	32.8343 mL	65.6685 mL
5 mM	1.3134 mL	6.5669 mL	13.1337 mL
10 mM	0.6567 mL	3.2834 mL	6.5669 mL

2,2’-Dithiobis(ethylamine), is a sulfur-rich, bifunctional amine-containing building block designed to connect recognition and E3-ligase-binding components through chemically addressable sites. Its disulfide-based functionality supports modular assembly strategies commonly used in targeted protein degradation workflows, offering practical handling and compatibility with standard linker-derivatization approaches. The structure and reactivity considerations are described in detail below.

Structure: The molecule contains a central disulfide linkage connecting two ethylamine units, providing two primary amine functionalities and a redox-active sulfur core. It features C–N and C–S/S–S bonding patterns that enable subsequent functional group interconversion while maintaining a defined, flexible scaffold.

Reactivity: Disulfide-containing linkers are typically leveraged for thiol/disulfide exchange or for controlled redox responsiveness during PROTAC synthesis and downstream conjugation steps. Primary amines can be activated for amide or urea formation using standard coupling chemistries, while disulfide exchange can proceed under mild, thiol-mediated conditions. Commonly used solvents include polar aprotic media and aqueous buffers compatible with amine coupling, with base and coupling reagents selected to preserve the disulfide integrity when required.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂