関: Tris buffer、tromethamine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/05/01 18:02:58」(JST)

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This article is about the chemical widely used as a biochemical buffer. For other uses, see Tris (disambiguation).

Tris (also known as THAM) is an abbreviation of the organic compound known as tris(hydroxymethyl)aminomethane, with the formula (HOCH₂)₃CNH₂. Tris is extensively used in biochemistry and molecular biology.^[1] In biochemistry, Tris is widely used as a component of buffer solutions, such as in TAE and TBE buffer, especially for solutions of nucleic acids. It is a primary amine and thus undergoes the reactions associated with typical amines, e.g. condensations with aldehydes.

Buffering features

Tris has a pK_a of 8.07 at 25 °C, which implies that the buffer has an effective pH range between 7.1 and 9.0.

Buffer details

The pK_a declines approximately 0.03 units per degree Celsius rise in temperature.^[2]^[3]
Silver-containing single-junction pH electrodes (e.g., silver chloride electrode) are incompatible with Tris (Ag-tris precipitation clogs the junction). Double-junction electrodes are resistant to this problem, and non-silver containing electrodes are immune.
When making buffer solutions by neutralizing TrisHCl requires attention to the attendant changes in ionic strength.

Buffer inhibition

Tris inhibits a number of enzymes,^[4]^[5] and therefore it should be used with care when studying proteins.

Preparation

Tris is prepared industrially in two steps from nitromethane via the intermediate (HOCH₂)₃CNO₂. Reduction of the latter gives tris(hydroxymethyl)aminomethane.^[6]

Uses

The useful buffer range for tris (7-9) coincides with the physiological pH typical of most living organisms. This, and its low cost, make tris one of the most common buffers in the biology/biochemistry laboratory. Tris is also used as a primary standard to standardize acid solutions for chemical analysis.

Medical

Tris (usually known as THAM in this context) is used as alternative to sodium bicarbonate in the treatment of metabolic acidosis.^[7]

Tris is one of the most widely used buffers in molecular biology and cell culture due to its low toxicity, stability and buffering capacity.

References

^ Gomori, G., Preparation of Buffers for Use in Enzyme Studies. Methods Enzymology., 1, 138-146 (1955).
^ El-Harakany, A.A.; Abdel Halima, F.M. and Barakat, A.O. (1984). "Dissociation constants and related thermodynamic quantities of the protonated acid form of tris-(hydroxymethyl)-aminomethane in mixtures of 2-methoxyethanol and water at different temperatures". J. Electroanal. Chem. 162 (1–2): 285–305. doi:10.1016/S0022-0728(84)80171-0.
^ Vega, C.A.; Butler, R.A. et al. (1985). "Thermodynamics of the Dissociation of Protonated Tris(hydroxymethy1)aminomethane in 25 and 50 wt % 2-Propanol from 5 to 45 °C". J. Chem. Eng. Data 30 (4): 376–379. doi:10.1021/je00042a003.
^ Desmarais, WT; et al. (2002). "The 1.20 Å resolution crystal structure of the aminopeptidase from Aeromonas proteolytica complexed with Tris: A tale of buffer inhibition". Structure 10 (8): 1063–1072. doi:10.1016/S0969-2126(02)00810-9. PMID 12176384.
^ Ghalanbor, Z; et al. (2008). "Binding of Tris to Bacillus licheniformis alpha-amylase can affect its starch hydrolysis activity". Protein Peptide Lett. 15 (2): 212–214. doi:10.2174/092986608783489616. PMID 18289113.
^ Markofsky, Sheldon B. (2000). Nitro Compounds, Aliphatic. doi:10.1002/14356007.a17_401.
^ Kallet, RH; Jasmer RM, Luce JM et al. (2000). "The treatment of acidosis in acute lung injury with tris-hydroxymethyl aminomethane (THAM)". American Journal of Respiratory and Critical Care Medicine 161 (4): 1149–1153. PMID 10764304.

UpToDate Contents

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English Journal

Development, evaluation and pharmacokinetics of time-dependent ketorolac tromethamine tablets.

Vemula SK, Veerareddy PR.SourceChaitanya College of Pharmacy Education and Research, Department of Pharmaceutics , Kishanpura, Hanamkonda, Warangal, Andhra Pradesh, 506001 , India +91 9989804999 ; vpreddyindia@gmail.com.
Expert opinion on drug delivery.Expert Opin Drug Deliv.2013 Jan;10(1):33-45. doi: 10.1517/17425247.2013.743528. Epub 2012 Nov 30.
Objective: The present study was intended to develop a time-dependent colon-targeted compression-coated tablets of ketorolac tromethamine (KTM) using hydroxypropyl methylcellulose (HPMC) that release the drug slowly but completely in the colonic region by retarding the drug releases in stomach and
PMID 23199134

Ketorolac tromethamine improves the analgesic effect of hyoscine butylbromide in patients with intense cramping pain from gastrointestinal or genitourinary origin.

Del Valle-Laisequilla CF, Flores-Murrieta FJ, Granados-Soto V, Rocha-González HI, Reyes-García G.SourceSección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional. Mexico, D.F., Mexico.
Arzneimittel-Forschung.Arzneimittelforschung.2012 Dec;62(12):603-8. doi: 10.1055/s-0032-1327678. Epub 2012 Oct 23.
The symptomatic treatment of pain associated with spasm of gastrointestinal or genitourinary origin can include the use of spasmolytic agents and/or non-steroidal anti-inflammatory drugs. However, the evidence of a superior effectiveness of combination in comparison with individual drugs is scarce a
PMID 23093479

A review of intranasal ketorolac tromethamine for the short-term management of moderate to moderately severe pain that requires analgesia at the opioid level.

He A, Hersh EV.SourcePost-Doctoral Fellow, College of Pharmacy and Health Sciences, St. John's University , Queens, New York; American Regent, Inc., Shirley, New York , USA.
Current medical research and opinion.Curr Med Res Opin.2012 Dec;28(12):1873-80. doi: 10.1185/03007995.2012.744302. Epub 2012 Nov 9.
Abstract Background: An intranasal (IN) formulation of ketorolac was recently FDA approved in adult patients for the short-term management of moderate to moderately severe pain that requires analgesia at the opioid level. Scope: The aim of this paper is to provide an overview of the clini
PMID 23098098

Japanese Journal

Preliminary Evaluation of Interactions between Selected Alcoholamines and Model Skin Sebum Components

MUSIAL Witold,KUBIS Aleksander
Chemical & pharmaceutical bulletin 54(8), 1076-1081, 2006-08-01
… The depth of aminomethyl-propendiol penetration increased with time from 0.148 to 4.064, respectively, of diisopropanolamine from 0.481 to 4.626, triethanolamine from 0.236 to 4.342, triisopropanolamine from 0.275 to 2.392 and trometamol from 0.338 to 4.580. …
NAID 110004847221

Trometamol による経皮的溶解療法が奏効した尿酸結石の1例

中川徹,遠藤文康,立川隆光,金子昌司,石井泰憲
西日本泌尿器科 59(5), 476-478, 1997-05-20
NAID 10019103650

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★リンクテーブル★

リンク元	「トロメタミン」「Tris buffer」「トロメタモル」

「トロメタミン」

Tris
	IUPAC name 2-Amino-2-hydroxymethyl-propane-1,3-diol
	Other names TRIS, Tris, Tris base, Tris buffer,; TrizmaTM, Trisamine, THAM,; Tromethamine, Trometamol, Tromethane, Trisaminol
Identifiers
CAS number	77-86-1
PubChem	6503
ChemSpider	6257
UNII	023C2WHX2V
KEGG	D00396
ChEBI	CHEBI:9754
ChEMBL	CHEMBL1200391
RTECS number	TY2900000
ATC code	B05BB03,B05XX02
Jmol-3D images	Image 1
	SMILES OCC(N)(CO)CO ;
	InChI InChI=1S/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2 ; Key: LENZDBCJOHFCAS-UHFFFAOYSA-N InChI=1/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2; Key: LENZDBCJOHFCAS-UHFFFAOYAN ;
Properties
Molecular formula	C4H11NO3
Molar mass	121.14 g mol−1
Appearance	White crystalline powder
Density	1.328g/cm3
Melting point	>175-176 °C (448-449 K)
Boiling point	219 °C, 492 K, 426 °F
Solubility in water	~50 g/100 mL (25 °C)
Acidity (pKa)	8.07
Hazards
MSDS	External MSDS
R-phrases	R36 R37 R38
S-phrases	S26 S36
Main hazards	Irritant
NFPA 704	0 2 0
Flash point	Non-flammable
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references