Tris (hydroxymethyl) aminomethane

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Structural formula
Structural formula of TRIS
General
Surname Tris (hydroxymethyl) aminomethane
other names
  • 2-amino-2- (hydroxymethyl) propane-1,3-diol
  • Trometamol ( INN )
  • Tromethamine
  • Tris
  • Trizma ®
  • TROMETHAMINE ( INCI )
Molecular formula C 4 H 11 NO 3
Brief description

colorless solid

External identifiers / databases
CAS number
EC number 201-064-4
ECHA InfoCard 100,000,969
PubChem 6503
ChemSpider 6257
DrugBank DB03754
Wikidata Q413961
Drug information
ATC code

B05 BB03 B05 XX02

Drug class

Acidosis therapeutic

properties
Molar mass 121.14 g mol −1
Physical state

firmly

density

1.35 g cm −3

Melting point
  • 172-173 ° C
  • 149 ° C (hydrochloride)
boiling point

219–220 ° C (at 1.33 kPa)

pK s value

8.2 (at 20 ° C)

solubility
  • good in water (800 g l −1 at 20 ° C) and ethanol
  • slightly soluble to insoluble in hydrocarbons
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
Toxicological data

5900 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tris (hydroxymethyl) aminomethane (short name TRIS ), also called tromethamine , trometamol ( INN ) and TRIS buffer . Chemically, it is a primary amine with three alcoholic hydroxyl groups .

synthesis

First, three moles of formaldehyde are added to nitromethane in an aldol reaction . The nitro group is then reduced to the amino group .

Chemical properties

Tris (hydroxymethyl) aminomethane is used as a buffer substance for biochemical, molecular biological, microbiological and pharmaceutical purposes . With a pK s 8.2 (at 20 ° C), TRIS has a good buffer capacity between pH 7.2-9.0. However, it shows a relatively strong temperature dependence of the acid constant (ΔpK s = −0.031 K −1 ). The pH value increases when the solution cools down or decreases when the solution is heated.

Determination of salary

The content of tris (hydroxymethyl) aminomethane can be determined as a weak base in an aqueous medium with methyl red as an indicator against hydrochloric acid . As an ethanolamine derivative, TRIS can be detected using the Chen-Kao reaction . The substance is mixed with sodium hydroxide solution and copper (II) sulfate (CuSO 4 ) (blue-violet color).

use

Buffer substance in biochemistry

The substance is a frequently used buffer substance in biochemistry, e.g. B. in the TE buffer for DNA purification or in electrophoresis buffers such as the separation of proteins by SDS-PAGE or the separation of nucleic acids by agarose gel electrophoresis ( TAE buffer , TBE buffer ). Tris (hydroxymethyl) aminomethane is also used for buffers to dissolve proteins, e.g. B. in TBS buffer and in TBS-T buffer . Since the compound has a reactive primary amino group , the buffer is unsuitable for some chemical applications, so Good buffers or inorganic buffers are used.

Excipient in pharmacy

Trometamol is used in various pharmaceutical dosage forms such as injection and infusion solutions, eye drops, creams and gels as an adjuvant for stabilization. It has an alkalizing and buffering effect.

Medicinal substance / buffer substance in medicine

In the form of its hydrochloride , tris (hydroxymethyl) aminomethane is used as a medicinal substance for the treatment of metabolic acidosis , and also to alkalize the urine in the case of poisoning with weakly acidic substances such as barbiturates . It is given intravenously. Since Tris-buffer has a respiratory depressive effect, its use in spontaneously breathing patients with respiratory insufficiency is contraindicated. As an organic base , tris (hydroxymethyl) aminomethane forms salts with mineral acids. Carbon dioxide (CO 2 ) dissolved in the blood can be neutralized in this way. At a physiological pH of 7.4, approx. 70% of the tris (hydroxymethyl) aminomethane in the blood plasma is ionized (= protonated ). Shape before. Non-ionized trometamol penetrates cell membranes and is also effective as a buffer intracellularly; this causes potassium shifts from the intracellular to the extracellular space. Initially, hyperkalemia and secondary hypokalaemia can occur. The compound's hydrochloride is available as a solution for infusion or a concentrate for infusion solution. The drug is only available on prescription in quantities of over 1 g per divided dosage form .

Trade names

Monopreparations

THAM (D), TRIS (D), as well as a generic (D)

See also

Individual evidence

  1. ↑ Entry on TROMETHAMINE in the CosIng database of the EU Commission, accessed on May 11, 2020.
  2. ↑ a b c d data sheet tris (hydroxymethyl) aminomethane (PDF) from Carl Roth , accessed on December 14, 2010.
  3. ↑ O. Piloty, O. Ruff: About some amino alcohols of the fatty series. In: Chem. Ber. 20, 1897, pp. 2057-2068, doi: 10.1002 / cber.189703002181 .
  4. ↑ a b c d Entry on trometamol. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
  5. ↑ a b Data sheet Tris (hydroxymethyl) aminomethane from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).
  6. ↑ Entry on tris (hydroxymethyl) aminomethane in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on November 15, 2016.
  7. ↑ New England Biolabs: Table with pH values ​​at different temperatures .