関: cysteamine、mercaptoethylamine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/08 23:25:33」(JST)

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Cysteamine 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 it exists in a salt form.^[1]

Preparation

It can also be prepared by the reaction of ethylenimine with hydrogen sulfide.^[1]

(NHCH₂CH₂) + H₂S → HSCH₂CH₂NH₂

Reactions

It 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

Biochemical and 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.^[2]

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.

References

^ ^a ^b Reid, E. Emmet (1958). Organic Chemistry of Bivalent Sulfur 1. New York: Chemical Publishing Company, Inc. pp. 398–399.
^ Lukashin BP, Grebeniuk AN (2001). "[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice]". Radiatsionnaia biologiia, radioecologiia / Rossiĭskaia akademiia nauk (in Russian) 41 (3): 310–2. PMID 11458646.

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English Journal

Chemical etching of bovine serum albumin-protected Au25 nanoclusters for label-free and separation-free detection of cysteamine.

Shu T1, Su L2, Wang J1, Li C3, Zhang X4.
Biosensors & bioelectronics.Biosens Bioelectron.2015 Apr 15;66:155-61. doi: 10.1016/j.bios.2014.10.073. Epub 2014 Nov 13.
This study describes a novel Au nanocluster-based fluorescent sensor for label-free, separation-free and selective detection of cysteamine (CSH). The sensing mechanism is based on CSH etching-induced fluorescence quenching of the bovine serum albumin-protected Au25 nanoclusters (BSAGNCs). A series o
PMID 25460897

MWCNT-cysteamine-Nafion modified gold electrode based on myoglobin for determination of hydrogen peroxide and nitrite.

Canbay E1, Sahin B2, Kıran M2, Akyilmaz E3.
Bioelectrochemistry (Amsterdam, Netherlands).Bioelectrochemistry.2015 Feb;101:126-31. doi: 10.1016/j.bioelechem.2014.09.001. Epub 2014 Sep 19.
In this work, a novel amperometric biosensor of hydrogen peroxide (H2O2) was developed based on the immobilization of myoglobin (Mb) on the surface of the multi-walled carbon nanotube (MWCNT) -Nafion-cysteamine (CA) modified gold electrode (Au) and its electrocatalytic activity was used for the dete
PMID 25262340

Reactive paper spray mass spectrometry for in situ identification of quinones.

Zhou X1, Pei J, Huang G.
Rapid communications in mass spectrometry : RCM.Rapid Commun Mass Spectrom.2015 Jan 15;29(1):100-6. doi: 10.1002/rcm.7092.
RATIONALE: The polycyclic aromatic hydrocarbons quinones are reported to be harmful and could cause mutations and cancer via the generation of reactive oxygen species through their redox cycle in human body. For detection by gas chromatography and high-performance liquid chromatography mass spectrom
PMID 25462369

「メルカプタミン」

Cysteamine
Names
	IUPAC name 2-aminoethanethiol
	Other names β-mercaptoethylamine; 2-aminoethanethiol; 2-mercaptoethylamine; decarboxycysteine; thioethanolamine; mercaptamine
Identifiers
CAS Registry Number	60-23-1 ; 156-57-0 (HCl)
ATC code	A16AA04; S01XA21
ChEBI	CHEBI:17141
ChEMBL	ChEMBL602
ChemSpider	5834
DrugBank	DB00847
	InChI InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2 ; Key: UFULAYFCSOUIOV-UHFFFAOYSA-N ; InChI=1/C2H7NS/c3-1-2-4/h4H,1-3H2; Key: UFULAYFCSOUIOV-UHFFFAOYAX ;
IUPHAR/BPS	7440
Jmol-3D images	Image
KEGG	D03634
PubChem	6058
	SMILES SCCN ;
UNII	5UX2SD1KE2
Properties
Chemical formula	C2H7NS
Molar mass	77.15 g·mol−1
Melting point	95 to 97 °C (203 to 207 °F; 368 to 370 K)
Hazards
Safety data sheet	External MSDS
EU classification (DSD)	Xn
S-phrases	S26 S36
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: mercaptamine
関: システアミン、メルカプトエチルアミン

「mercaptoethylamine」

　　[★]

メルカプトエチルアミン

関: cysteamine、mercaptamine

「cysteamine」

　　[★]

システアミン

関: mercaptamine、mercaptoethylamine

[Reid-1] Reid, E. Emmet (1958). Organic Chemistry of Bivalent Sulfur 1. New York: Chemical Publishing Company, Inc. pp. 398–399.

[pmid11458646-2] Lukashin BP, Grebeniuk AN (2001). "[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice]". Radiatsionnaia biologiia, radioecologiia / Rossiĭskaia akademiia nauk (in Russian) 41 (3): 310–2. PMID 11458646.

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mercaptamine