システアミン
- 関
- mercaptamine、mercaptoethylamine
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/10/22 13:48:58」(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 |
CAS Registry Number
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60-23-1 Y
156-57-0 (HCl) Y |
ATC code |
A16AA04
S01XA21 |
ChEBI |
CHEBI:17141 Y |
ChEMBL |
ChEMBL602 Y |
ChemSpider |
5834 Y |
DrugBank |
DB00847 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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IUPHAR/BPS
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7440 |
Jmol-3D images |
Image |
KEGG |
D03634 Y |
PubChem |
6058 |
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UNII |
5UX2SD1KE2 Y |
Properties |
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) |
Hazards |
Safety data sheet |
External MSDS |
EU classification |
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: Y/N?) |
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.
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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UpToDate Contents
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English Journal
- Construction of novel electrochemical immunosensor for detection of prostate specific antigen using ferrocene-PAMAM dendrimers.
- Çevik E1, Bahar Ö2, Şenel M3, Abasıyanık MF2.
- Biosensors & bioelectronics.Biosens Bioelectron.2016 Dec 15;86:1074-9. doi: 10.1016/j.bios.2016.07.064. Epub 2016 Jul 20.
- In this study, an immunosensor was designed to utilize for the detection of prostate specific antigen (PSA) based on three different generations (G1, G2 and G3) of ferrocene (Fc) cored polyamidiamine dendrimers (Fc-PAMAM) gold (Au) electrode. The self-assembled monolayer principle (SAM) was used to
- PMID 27641479
- Cysteamine capped CdS quantum dots as a fluorescence sensor for the determination of copper ion exploiting fluorescence enhancement and long-wave spectral shifts.
- Boonmee C1, Noipa T2, Tuntulani T3, Ngeontae W4.
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2016 Dec 5;169:161-8. doi: 10.1016/j.saa.2016.05.007. Epub 2016 May 8.
- We described a turn-on fluorescence sensor for the determination of Cu(2+) ions, utilizing the quantum confinement effect of cadmium sulfide quantum dots capped with cysteamine (Cys-CdS QDs). The fluorescence intensity of the Cys-CdS QDs was both enhanced and red shifted (from blue-green to yellow)
- PMID 27372512
- Manipulating proteostasis to repair the F508del-CFTR defect in cystic fibrosis.
- Esposito S1, Tosco A2, Villella VR1, Raia V3, Kroemer G4,5,6,7,8,9,10, Maiuri L11,12.
- Molecular and cellular pediatrics.Mol Cell Pediatr.2016 Dec;3(1):13. doi: 10.1186/s40348-016-0040-z. Epub 2016 Mar 14.
- Cystic fibrosis (CF) is a lethal monogenic disease caused by mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) gene that entails the (diagnostic) increase in sweat electrolyte concentrations, progressive lung disease with chronic inflammation and recurrent bacterial infecti
- PMID 26976279
Japanese Journal
- Electrochemical Determination of Dopamine in the Presence of Ascorbic Acid and Uric Acid Using the Synergistic Effect of Gold Nanoflowers and L-Cysteamine Monolayer at the Surface of a Gold Electrode
- Li Yongxin,Lu Qiufang,Shi Aibin [他],CHEN Yuanli,WU Shengnan,WANG Lun
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 27(9), 921-927, 2011-09-10
- NAID 10029761107
- Identification of N-homocysteinylated apolipoprotein AI in normal human serum
- Ishimine N,Usami Y,Nogi S,Sumida T,Kurihara Y,Matsuda K,Nakamura K,Yamauchi K,Okumura N,Tozuka M,山内 一由
- Annals of clinical biochemistry 47, 453-459, 2010-09-00
- … The present study strives to develop detection and potential semi-quantification methods for N-homocysteinylated apolipoprotein AI (N-Hcy-apoAI) in human serum.Methods: Serum treated with or without cysteamine was supplied to isoelectric focusing (IEF) followed by an immunoblot using an anti-apoAI antibody. … Cysteamine treatment increased the isoelectric point for N-Hcy-apoAI, but not for unmodified apoAI, due to the presence of -SH group(s) derived from Hcy and the absence of a cysteine residue in the apoAI molecule. …
- NAID 120002598897
- Intestinal Metaplasia : The Effect of Acid on the Gastric Mucosa and Gastric Carcinogenesis
- Watanabe Hiromitsu,ワタナベ ヒロミツ,渡邊 敦光
- Journal of toxicologic pathology 23(3), 115-123, 2010
- … Alkaline phosphatase (ALP) positive metaplastic foci were increased by administration of ranitidine (H2 receptor antagonist), crude stomach antigens or subtotal resection of the fundus and decreased by cysteamine (gastric acid secretion stimulator), histamine or removal of the submandibular glands. …
- NAID 130000450737
Related Links
- Sigma-Aldrich offers Aldrich-M9768, Cysteamine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... ANALYTICAL / CHROMATOGRAPHY » Analytical Standards Gas ...
- Sigma-Aldrich offers Sigma-M6500, Cysteamine hydrochloride for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Packaging 25, 100 g in glass bottle
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★リンクテーブル★
[★]
- 英
- cysteamine
- 関
- メルカプタミン、メルカプトエチルアミン
[★]
メルカプトエチルアミン
- 関
- cysteamine、mercaptamine
[★]
メルカプタミン
- 関
- cysteamine、mercaptoethylamine