メルカプトエチルアミン
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- cysteamine、mercaptamine
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/22 09:27:18」(JST)
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Not to be confused with cystamine.
Cysteamine
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| Names |
| IUPAC name
2-aminoethanethiol
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Other names
β-mercaptoethylamine
2-aminoethanethiol
2-mercaptoethylamine
decarboxycysteine
thioethanolamine
mercaptamine
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| Identifiers |
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CAS Number
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60-23-1 Y
156-57-0 (HCl) Y |
| ChEBI |
CHEBI:17141 Y |
| ChEMBL |
ChEMBL602 Y |
| ChemSpider |
5834 Y |
| DrugBank |
DB00847 Y |
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IUPHAR/BPS
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7440 |
| Jmol interactive 3D |
Image |
| KEGG |
D03634 Y |
| PubChem |
6058 |
| UNII |
5UX2SD1KE2 Y |
InChI
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InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2 Y
Key: UFULAYFCSOUIOV-UHFFFAOYSA-N Y
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InChI=1/C2H7NS/c3-1-2-4/h4H,1-3H2
Key: UFULAYFCSOUIOV-UHFFFAOYAX
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| Properties |
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Chemical formula
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C2H7NS |
| Molar mass |
77.15 g·mol−1 |
| Melting point |
95 to 97 °C (203 to 207 °F; 368 to 370 K) |
| Pharmacology |
| ATC code |
A16AA04
S01XA21 |
| Hazards |
| Safety data sheet |
External MSDS |
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EU classification (DSD)
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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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| Y verify (what is YN ?) |
| Infobox references |
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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]
Contents
- 1 Preparation
- 2 Reactions
- 3 Biochemical and pharmaceutical applications
- 4 References
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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Other alimentary tract and metabolism products (A16)
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| Amino acids and derivatives |
- Levocarnitine
- Ademetionine
- Levoglutamide
- Cysteamine
- Carglumic acid
- Betaine
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| Enzymes |
- Carbohydrate metabolism: sucrase (Sacrosidase)
- alpha-glucosidase (Alglucosidase alfa)
- Glycolipid/sphingolipid: glucocerebrosidase (Alglucerase
- Imiglucerase
- Taliglucerase alfa
- Velaglucerase alfa)
- alpha-galactosidase (Agalsidase alfa
- Agalsidase beta)
- Glycosaminoglycan: iduronidase (Laronidase)
- arylsulfatase B (Galsulfase)
- iduronate-2-sulfatase (Idursulfase)
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| Other |
- Anethole trithione
- Eliglustat
- Glycerol phenylbutyrate
- Miglustat
- Nitisinone
- Sapropterin
- Sodium phenylbutyrate
- Teduglutide
- Tioctic acid
- Zinc acetate
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Index of digestion
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| Description |
- Anatomy
- Physiology
- Development
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| Disease |
- Congenital
- Neoplasms and cancer
- Inflammatory bowel disease
- Gluten sensitivity
- Other
- Symptoms and signs
- Blood tests
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| Treatment |
- Procedures
- Drugs
- anabolic steroids
- antacids
- diarrhoea and infection
- bile and liver
- functional gastrointestinal disorders
- laxatives
- peptic ulcer and reflux
- nausea and vomiting
- other
- Surgery
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English Journal
- Tailored carbon nanotube immunosensors for the detection of microbial contamination.
- Prieto-Simón B1, Bandaru NM2, Saint C3, Voelcker NH4.
- Biosensors & bioelectronics.Biosens Bioelectron.2015 May 15;67:642-8. doi: 10.1016/j.bios.2014.09.089. Epub 2014 Oct 5.
- The use of carbon nanotubes (CNTs) as building blocks in the design of electrochemical biosensors has been attracting attention over the last few years, mainly due to their high electrical conductivity and large surface area. Here, we present two approaches based on tailored single-walled CNTs (SWCN
- PMID 25316087
- Highly enhanced adsorption for the removal of Hg(II) from aqueous solution by Mercaptoethylamine/Mercaptopropyltrimethoxysilane functionalized vermiculites.
- Tran L1, Wu P2, Zhu Y3, Yang L3, Zhu N3.
- Journal of colloid and interface science.J Colloid Interface Sci.2015 May 1;445:348-56. doi: 10.1016/j.jcis.2015.01.006. Epub 2015 Jan 13.
- Vermiculites modified with Mercaptoethylamine (MEA) and 3-Mercaptopropyltrimethoxysilane (MPTMS) were used as effective adsorbents for the removal of Hg(II) from aqueous solution. The physicochemical characteristics of the pristine and functionalized vermiculites were analyzed by XRD, BET, FTIR, SEM
- PMID 25643962
- 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
Japanese Journal
- Dihydropyrazine-Induced Inactivation of Glyceraldehyde-3-phosphate Dehydrogenase
- Takechi Shinji,Nakahara Kazuhide,Yamaguchi Tadatoshi
- Biological & Pharmaceutical Bulletin 33(3), 379-383, 2010
- … SH-compounds, such as cysteine, dithiothreitol (DTT), 2-mercaptoethanol, 2-mercaptoethylamine, and N-acetyl-cysteine, suppressed the inhibition of GAPDH by DHP in vitro, although the effect of DHP on GAPDH was not reversed by DTT. …
- NAID 130000248085
- Hypohomocysteinemic Effect of Cysteine Is Associated with Increased Plasma Cysteine Concentration in Rats Fed Diets Low in Protein and Methionine Levels
- KAWAKAMI Yoshiko,OHUCHI Seiya,MORITA Tatsuya,SUGIYAMA Kimio
- Journal of nutritional science and vitaminology 55(1), 66-74, 2009-02
- … Unlike cysteine, cysteic acid and 2-mercaptoethylamine did not decrease plasma homocysteine concentration. …
- NAID 110007110603
Related Links
- Thermo Scientific Pierce 2-Mercaptoethylamine-HCl, commonly abbreviated 2-MEA, is a mild reductant that is often used to selectively reduce hinge-region disulfide bonds in antibody. ... This item is not currently available on-site.
- INSTRUCTIONS Pierce Biotechnology PO Box 117 (815) 968-0747 www.thermo.com/pierce 3747 N. Meridian Road Rockford, lL 61105 USA (815) 968-7316 fax Number Description 20408 2-Mercaptoethylamine•HCl (2-MEA), 6 × 6 mg in amber screw-cap vials
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- mercaptoethylamine
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- システアミン、メルカプタミン
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メルカプタミン
- 関
- cysteamine、mercaptoethylamine
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システアミン
- 関
- mercaptamine、mercaptoethylamine