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the 20th letter of the Roman alphabet (同)t
any of several compounds containing chlorine and nitrogen; used as an antiseptic in wounds (同)chloramine-T
a tough youth of 1950s and 1960s wearing Edwardian style clothes (同)Teddy boy

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/12/26 11:39:41」(JST)

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Tosylchloramide or N-chloro tosylamide, sodium salt, sold as chloramine-T, is a N-chlorinated and N-deprotonated sulfonamide used as a biocide and a mild disinfectant. It is a white powder that gives unstable solutions with water. Trade names of chloramine-T products include Chloraseptin, Chlorazol, Clorina, Disifin, Halamid, Hydroclonazone, Trichlorol, Minachlor, and generic Chloramin T or Tosylchloramide Sodium, among others.

Chemistry

As an N-chloro compound, it contains active (electrophilic) chlorine and can be compared to the O-chlorinated sodium hypochlorite. Chloramine-T is slightly basic (pH typically 8.5). In water, it breaks down to the disinfectant hypochlorite. It can be used as a source of electrophilic chlorine in organic synthesis.

The anionic sulfonamide is stabilized by delocalization of the nitrogen lone pair across the SO₂ group, facilitating deprotonation of the parent amine by bases such as hydroxide. It is readily biodegradable by use of ultraviolet (UV) light.

Synthesis

Chloramine-T is prepared from p-toluenesulfonamide and sodium hypochlorite, with the latter being produced in situ from sodium hydroxide and chlorine (Cl₂).^[1]

Uses

Iodination and radioiodination

Hypochlorite released from chloramine-T acts as an effective oxidizing agent for iodide to form iodine monochloride (ICl). ICl rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid tyrosine. Thus, chloramine-T is widely used for the incorporation of iodine to peptides and proteins. Chloramine-T together with iodogen or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes (¹²³I, ¹²⁵I or ¹³¹I).^[2]

Biocide

Chloramine-T is available in tablet or powder form and has to be dissolved before use. It is sprayed on a surface and allowed to stand for at least 15 minutes before being wiped off or allowed to dry. It used in areas such as hospitals, laboratories, nursing homes, funeral homes, medical, dental and veterinary facilities, where control of pathogens is required, for disinfecting surfaces and soaking medical and dental equipment. The substance is also used for parasite control and for drinking water disinfection.

Chloramine-T is as an algicide, bactericide, virucide, fungicide (including spores), germicide. It is also effective against mycobacteria such as tuberculosis, foot-and-mouth disease and avian influenza. The molecular structure of toluenesulfonylamide is similar to para-aminobenzoic acid, an intermediate in bacterial metabolism, which is disrupted by this sulfonamide (in the same way as by a sulfa drug). Therefore, chloramine-T is capable of inhibiting with bacterial growth with two mechanisms, with the phenylsulfonamide moiety and the hypochlorite, which destroys the DNA structure via oxidation and thereby prevents microbes from reproducing and reforming.

Protective agent

Chloramine-T reacts readily with mustard gas to yield a harmless crystalline sulfimide; chloramine-T derivatives are being studied as protective agents against poison gas.^[3]

Certifications

EN 1276 Bactericidal
EN 13713 Bactericidal
EN 14675 Virucidal
EN 14476 Virucidal Norovirus
EN 1650 Fungicidal
EN 13704 Sporicidal Clostridium difficile

References

^ M. Shetty, T. B. Gowda, A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium, in: Zeitschrift für Naturforschung 2004, 59, 63–72.
^ F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4. Dordrecht/Boston/London: Kluwer Academic Publishers.
^ Yasukazu Ura; Gozyo Sakata (2007), "Chloroamines", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5

External links

Chemicalland21.com: Chloramine T (Tosylchloramide sodium)
InChem.org: Chloramine T
"Disifin USA". Retrieved 2010-02-09.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 血液透析に使用される水の混入物質 contaminants in water used for hemodialysis
2. 血液透析における水の浄化システム water purification systems in hemodialysis
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5. 血液透析装置の概要 overview of the hemodialysis apparatus

English Journal

Analysis of amino acid composition in proteins of animal tissues and foods as pre-column o-phthaldialdehyde derivatives by HPLC with fluorescence detection.

Dai Z1, Wu Z1, Jia S2, Wu G3.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2014 Aug 1;964C:116-127. doi: 10.1016/j.jchromb.2014.03.025. Epub 2014 Mar 31.
Studies of protein nutrition and biochemistry require reliable methods for analysis of amino acid (AA) composition in polypeptides of animal tissues and foods. Proteins are hydrolyzed by 6M HCl (110°C for 24h), 4.2M NaOH (105°C for 20h), or proteases. Analytical techniques that require high-perfor
PMID 24731621

Chlorosulfonamide salts are superior electrophilic chlorine precursors for the organocatalytic asymmetric chlorocyclization of unsaturated amides.

Jaganathan A1, Borhan B.
Organic letters.Org Lett.2014 Jul 18;16(14):3616-9. doi: 10.1021/ol500861z. Epub 2014 Jun 30.
Chloramine-T·3H2O and other chlorosulfonamide salts can serve as readily available, stable, and inexpensive precursors of electrophilic chlorine in the organocatalytic asymmetric chlorofunctionalization of olefins. In conjunction with commercially available organocatalysts, they can be utilized in
PMID 24979487

Nanocarriers and the delivered drug: Effect interference due to intravenous administration.

Vlasova MA1, Rytkönen J2, Riikonen J3, Tarasova OS4, Mönkäre J2, Kovalainen M2, Närvänen A2, Salonen J5, Herzig KH6, Lehto VP7, Järvinen K8.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2014 Jun 22. pii: S0928-0987(14)00271-1. doi: 10.1016/j.ejps.2014.06.011. [Epub ahead of print]
Intravenously administered nanocarriers are widely studied to improve the delivery of various therapeutic agents. However, recent in vivo studies have demonstrated that intravenously administered nanocarriers that do not contain any drug may affect cardiovascular function. Here we provide an example
PMID 24964293

Japanese Journal

文献抄録急速なクロラミン減少と微生物の再増殖に及ぼす先進的な節水と新しい銅管の影響

水道協会雑誌 83(11), 28-30, 2014-11
NAID 40020264794

Characterization of vitamin B₁₂ compounds in the fruiting bodies of shiitake mushroom (Lentinula edodes) and bed logs after fruiting of the mushroom

Mycoscience : official journal of the Mycological Society of Japan 55(6), 462-468, 2014-11
NAID 40020205766

Microarray gene expression analysis of Monochamus alternatus (Coleoptera : Cerambycidae) after treatment with a sublethal dose of chloramine phosphorus

Applied entomology and zoology 49(2), 223-230, 2014-05
NAID 40020070394

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関連記事	「T」「chloramine」

「T」

Chloramine-T
	IUPAC name N-chloro 4-methylbenzenesulfonamide, sodium salt
	Other names N-chloro para-toluenesulfonylamide,; sodium chloro[(4-methyl phenyl)sulfonyl]azanide, chloramine-T
Identifiers
CAS number	127-65-1 , 7080-50-4 (trihydrate)
PubChem	10198484, 31388 (free acid)
ChemSpider	2876055 , 29119 (free acid)
UNII	328AS34YM6 , 4IU6VSV0EI (trihydrate)
KEGG	D02445
ChEBI	CHEBI:53782
ChEMBL	CHEMBL1697734
ATC code	D08AX04,QP53AB04
Jmol-3D images	Image 1
	SMILES [Na+].O=S(=O)([N-]Cl)c1ccc(cc1)C ;
	InChI InChI=1S/C7H8ClNO2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,1H3 ; Key: NXTVQNIVUKXOIL-UHFFFAOYSA-N InChI=1/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1; Key: VDQQXEISLMTGAB-UHFFFAOYAP ;
Properties
Molecular formula	C7H7ClNO2S·Na (3H2O)
Molar mass	227.64 g/mol in usual tri-hydrated form 282 Daltons.
Appearance	white powder
Density	1.4 g/cm³
Melting point	releases chlorine at 130 °C; solid melts at 167–169 °C
Solubility in water	15% in water (25 °C); 7.5% in rectified spirit (20 °C); insoluble in benzene and ethers
Hazards
R-phrases	R22 R31 R34 R42
S-phrases	(S1/2) S7 S22 S26 S36/37/39 S45
Main hazards	Corrosive
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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「chloramine」

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関: monochloramine

[shetty-1] M. Shetty, T. B. Gowda, A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium, in: Zeitschrift für Naturforschung 2004, 59, 63–72.

[Radiochemistry-2] F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4. Dordrecht/Boston/London: Kluwer Academic Publishers.

[ueoic-3] Yasukazu Ura; Gozyo Sakata (2007), "Chloroamines", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5

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chloramine T