60-23-1 Usage
Description
2-AMINOETHANETHIOL is the chemical compound with the formula HSCH2CH2NH2. It is the simplest stable aminothiol and a degradation product of the amino acid cysteine. It is often used as the hydrochloride salt, HSCH2CH2NH3Cl. The comparatively high melting point of cysteamine (95-97 °C), indicates that exists in a salt form.
Chemical Properties
2-AMINOETHANETHIOL is white powder
Uses
Different sources of media describe the Uses of 60-23-1 differently. You can refer to the following data:
1. antihyperlipidemic, HMGCoA reductase inhibitor
2. Scavenges benzyl and allyl halides and ketones.
3. Cysteamine is suitable for use:in the preparation of cysteamine modified gold nanoparticles (AuNP)in the fabrication of SU-8 microrods, where in, the amine group of cysteamine reacts with the unreacted epoxide rings present on the surface of the particles, thereby opening it and forming a covalent bondto enhance in vitro development of porcine oocytes matured and fertilized in vitroin a study to demonstrate the depletion effect of cysteamine on cystinotic leucocyte granular fractions of cystine by disulphide interchangeas a radioprotectorto administer subcutaneously in rats to study its blocking effect on somatostatin secretion without modifying the pancreatic insulin or glucagon content as a scavenger in electrophoretic gels (acetic acid/urea gels)
4. 2-Aminoethanethiol is used in preparation method of fluorescence quenching array sensor based on cadmium telluride quantum dots and application in qualitative discrimination and quantitative analysis of organic acids.
Definition
2-AMINOETHANETHIOL is an amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.
Preparation
Cysteamine can also be prepared by the reaction of ethylenimine with hydrogen sulfide. (NHCH2CH2) + H2S → HSCH2CH2NH2.
Reactions
2-AMINOETHANETHIOL is used as the hydrochloride salt, as it readily oxidizes to the corresponding disulfide, in the presence of air. The amine portion of the molecule serves as a catalyst for this reaction.
4 HSCH2CH2NH2 + O2 → 2 NH2CH2CH2SSCH2CH2NH2 + 2 H2O.
Pharmaceutical Applications
Under the trade name Cystagon, cysteamine is used in the treatment of disorders of cystine excretion. Cysteamine cleaves the disulfide bond with cystine to produce molecules that can escape the metabolic defect in cystinosis and cystinuria. It is also used for treatment of radiation sickness. Cysteamine is used in the body to form the essential biochemical coenzyme A by combining with pantothenate and adenosine triphosphate. In 2008, Raptor Pharmaceuticals started phase II clinical trials testing a delayed release (DR) preparation of cysteamine bitartrate for Huntington's disease. DR Cysteamine is also being investigated as a treatment for cystinosis, Batten disease, and non-alcoholic steatohepatitis.
Biochem/physiol Actions
Cysteamine (β-mercaptoethylamine) depletes cystine from patient′s cells and there by regulates renal glomerular function and increases growth in them. Therefore, cysteamine is considered to be a potential therapeutic for nephropathic cystinosis.
Safety Profile
Poison by intravenous, subcutaneous, and intraperitoneal routesModerately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of SO, and NOx,.
Purification Methods
It is soluble in H2O giving an alkaline reaction, and it has a disagreeable odour. A likely impurity is the disulfide cystamine which is not soluble in alkaline solution. Under a N2 atmosphere dissolve it in EtOH, evaporate to dryness and wash the white residue with dry pet ether, then sublime it at 0.1mm and store it under N2 at 0-10o in the dark. Its HgCl2 (2:3) complex has m 181-182o (from H2O), and its picrate has m 125-126o. [Mills & Bogert J Am Chem Soc 57 2328 1935, 62 1173 1940, Baddiley & Thain J Chem Soc 800 1952, Shirley Preparation of Organic Intermediates (J. Wiley) Vol 3 189 1951, Barkowski & Hedberg J Am Chem Soc 109 6989 1987, Beilstein 4 IV 1570.]
Check Digit Verification of cas no
The CAS Registry Mumber 60-23-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 60-23:
(4*6)+(3*0)+(2*2)+(1*3)=31
31 % 10 = 1
So 60-23-1 is a valid CAS Registry Number.
InChI:InChI=1/C2H6NS/c3-1-2-4/h1-3H2
60-23-1Relevant articles and documents
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Gaul,Fremuth
, p. 869 (1960)
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"dual Layer" Self-Sorting with Cucurbiturils
Barbero, Héctor,Masson, Eric,Thompson, Nathan A.
, p. 867 - 873 (2020)
Platinum(II) complexes bearing terpyridyl (tpy) and thiolate ligands were used to test the design of a "dual layer" self-sorting system in the presence of Cucurbit[8]uril (CB[8]). Pt(II) thiolates and CB[8] form 2:1 assemblies, with both metallic centers sitting on top of one another at one of the macrocycle portals. We showed that any pair of these CB[8]-secured Pt(II) complex dimers bearing different tpy "heads" and thiolate "tails" scrambles to afford up to 10 ternary assemblies via two processes: (1) supramolecular exchanges (i.e., the egression and ingression of Pt complexes from and into CB[8]) and (2) ligand exchanges between the Pt thiolates. The mixtures of 10 assemblies were fully characterized by nuclear magnetic resonance spectroscopy. While the thiolate tails do not significantly affect the rate of the supramolecular exchanges, they were found to control (1) the kinetics of ligand exchange, with bulkier thiolates causing dramatic rate retardations, as well as (2) the thermodynamics of the self-sorting process, i.e., the distribution of assemblies at equilibrium, via intra-CB[8] assembly interactions between pairs of thiolates. Ligand exchanges are consistently slower than supramolecular exchanges. An associative pathway that involves the formation of dimers of CB[8]-secured Pt dimers (a total of 4 Pt complexes) during the ligand exchange process was invoked to rationalize the observed kinetics.
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Voronkov,M.G. et al.
, (1979)
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Non-specific reaction inhibitor, method for inhibiting non-specific reaction, and kit
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, (2021/09/22)
Provided is a non-specific reaction inhibitor for achieving the accurate detection and quantitation of a trace component (a target substance) contained in a sample, in an immunoassay, by simply and effectively inhibiting a non-specific reaction associated with the measurement. The non-specific reaction inhibitor comprises a substance of the formula I: wherein R1 and R2 together form a double bond between carbons, to which they are respectively bonded directly, or R1 is a hydrogen atom and R2 is a group formed by removing H from an SH-group-containing compound, B is a support, and L is a spacer arm portion.
Engineering a cleavable disulfide bond into a natural product siderophore using precursor-directed biosynthesis
Richardson-Sanchez, Tomas,Codd, Rachel
supporting information, p. 9813 - 9816 (2018/09/10)
An analogue of the bacterial siderophore desferrioxamine B (DFOB) containing a disulfide motif in the backbone was produced from Streptomyces pilosus cultures supplemented with cystamine. Cystamine competed against native 1,5-diaminopentane during assembly. DFOB-(SS)1[001] and its complexes with Fe(iii) or Ga(iii) were cleaved upon incubation with dithiothreitol. Compounds such as DFOB-(SS)1[001] and its thiol-containing cleavage products could expand antibiotic strategies and Au-S-based nanotechnologies.
