Tris

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Tris
2-amino-2-(hydroxymethyl)propane-1,3-diol 200.svg
Names
Preferred IUPAC name
2-Amino-2-(hydroxymethyl)propane-1,3-diol
Other names
TRIS, Tris, Tris base, Tris buffer, Trizma, Trisamine, THAM, Tromethamine, Trometamol, Tromethane, Trisaminol, Tris(hydroxymethyl)aminomethane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.969 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-064-4
KEGG
PubChem CID
RTECS number
  • TY2900000
UNII
  • InChI=1S/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2 Yes check.svgY
    Key: LENZDBCJOHFCAS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2
    Key: LENZDBCJOHFCAS-UHFFFAOYAN
  • OCC(N)(CO)CO
Properties
C4H11NO3
Molar mass 121.136 g·mol−1
AppearanceWhite crystalline powder
Density 1.328g/cm3
Melting point >175-176 °C (448-449 K)
Boiling point 219 °C (426 °F; 492 K)
~50 g/100 mL (25 °C)
Acidity (pKa)8.07 (conjugate acid)
Pharmacology
B05BB03 ( WHO ) B05XX02 ( WHO )
Hazards [1]
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P362, P403+P233, P405
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
2
Flash point Non-flammable
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Tris, or tris(hydroxymethyl)aminomethane, or known during medical use as tromethamine or THAM, is an organic compound with the formula (HOCH2)3CNH2. It is extensively used in biochemistry and molecular biology as a component of buffer solutions [2] such as in TAE and TBE buffers, especially for solutions of nucleic acids. It contains a primary amine and thus undergoes the reactions associated with typical amines, e.g., condensations with aldehydes. Tris also complexes with metal ions in solution. [3] In medicine, tromethamine is occasionally used as a drug, given in intensive care for its properties as a buffer for the treatment of severe metabolic acidosis in specific circumstances. [4] [5] Some medications are formulated as the "tromethamine salt" including Hemabate (carboprost as trometamol salt), and "ketorolac trometamol". [6] In 2023 a strain of Pseudomonas hunanensis was found to be able to degrade TRIS buffer. [7]

Buffering features

The conjugate acid of tris has a pKa of 8.07 at 25 °C, which implies that the buffer has an effective pH range between 7.1 and 9.1 (pKa ± 1) at room temperature.

Buffer details

Buffer inhibition

Preparation

Tris is prepared industrially by the exhaustive condensation of nitromethane with formaldehyde under basic conditions (i.e. repeated Henry reactions) to produce the intermediate (HOCH2)3CNO2, which is subsequently hydrogenated to give the final product. [11]

Uses

The useful buffer range for tris (pH 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.

Tris is used to increase permeability of cell membranes. [12] It is a component of the Moderna COVID-19 vaccine [13] and the Pfizer-BioNTech COVID-19 vaccine for use in children 5 through 11 years of age. [14]

Medical

Tris (usually known as THAM in this context) is used as alternative to sodium bicarbonate in the treatment of metabolic acidosis. [15] [16]

See also

Related Research Articles

<span class="mw-page-title-main">Carbonate</span> Salt or ester of carbonic acid

A carbonate is a salt of carbonic acid, H2CO3, characterized by the presence of the carbonate ion, a polyatomic ion with the formula CO2−3. The word "carbonate" may also refer to a carbonate ester, an organic compound containing the carbonate groupO=C(−O−)2.

pH Measure of the level of acidity or basicity of an aqueous solution

In chemistry, pH, also referred to as acidity or basicity, historically denotes "potential of hydrogen". It is a logarithmic scale used to specify the acidity or basicity of aqueous solutions. Acidic solutions are measured to have lower pH values than basic or alkaline solutions.

<span class="mw-page-title-main">Citric acid</span> Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

<span class="mw-page-title-main">Lactic acidosis</span> Metabolic medical condition

Lactic acidosis is a medical condition characterized by a build-up of lactate in the body, with formation of an excessively low pH in the bloodstream. It is a form of metabolic acidosis, in which excessive acid accumulates due to a problem with the body's oxidative metabolism.

Acidosis is a process causing increased acidity in the blood and other body tissues. If not further qualified, it usually refers to acidity of the blood plasma.

A lysis buffer is a buffer solution used for the purpose of breaking open cells for use in molecular biology experiments that analyze the labile macromolecules of the cells. Most lysis buffers contain buffering salts and ionic salts to regulate the pH and osmolarity of the lysate. Sometimes detergents are added to break up membrane structures. For lysis buffers targeted at protein extraction, protease inhibitors are often included, and in difficult cases may be almost required. Lysis buffers can be used on both animal and plant tissue cells.

<span class="mw-page-title-main">Metabolic acidosis</span> Medical condition

Metabolic acidosis is a serious electrolyte disorder characterized by an imbalance in the body's acid-base balance. Metabolic acidosis has three main root causes: increased acid production, loss of bicarbonate, and a reduced ability of the kidneys to excrete excess acids. Metabolic acidosis can lead to acidemia, which is defined as arterial blood pH that is lower than 7.35. Acidemia and acidosis are not mutually exclusive – pH and hydrogen ion concentrations also depend on the coexistence of other acid-base disorders; therefore, pH levels in people with metabolic acidosis can range from low to high.

<span class="mw-page-title-main">Ringer's lactate solution</span> Fluid used for resuscitation after blood loss

Ringer's lactate solution (RL), also known as sodium lactate solution,Lactated Ringer's, and Hartmann's solution, is a mixture of sodium chloride, sodium lactate, potassium chloride, and calcium chloride in water. It is used for replacing fluids and electrolytes in those who have low blood volume or low blood pressure. It may also be used to treat metabolic acidosis and to wash the eye following a chemical burn. It is given by intravenous infusion or applied to the affected area.

The anion gap is a value calculated from the results of multiple individual medical lab tests. It may be reported with the results of an electrolyte panel, which is often performed as part of a comprehensive metabolic panel.

<span class="mw-page-title-main">Bis-tris propane</span> Chemical compound

Bis-tris propane, or 1,3-bis(tris methylamino)propane, also known as BTP, is a chemical substance that is used in buffer solutions. It is a white to off-white crystalline powder that is soluble in water. It has a wide buffering range, from 6 to 9.5 due to its two pKa values which are close in value. This buffer is primarily used in biochemistry and molecular biology.

<span class="mw-page-title-main">Metabolic alkalosis</span> Medical condition

Metabolic alkalosis is a metabolic condition in which the pH of tissue is elevated beyond the normal range (7.35–7.45). This is the result of decreased hydrogen ion concentration, leading to increased bicarbonate, or alternatively a direct result of increased bicarbonate concentrations. The condition typically cannot last long if the kidneys are functioning properly.

<span class="mw-page-title-main">Carbonic anhydrase inhibitor</span> Class of pharmaceuticals

Carbonic anhydrase inhibitors are a class of pharmaceuticals that suppress the activity of carbonic anhydrase. Their clinical use has been established as anti-glaucoma agents, diuretics, antiepileptics, in the management of mountain sickness, gastric and duodenal ulcers, idiopathic intracranial hypertension, neurological disorders, or osteoporosis.

Acid–base homeostasis is the homeostatic regulation of the pH of the body's extracellular fluid (ECF). The proper balance between the acids and bases in the ECF is crucial for the normal physiology of the body—and for cellular metabolism. The pH of the intracellular fluid and the extracellular fluid need to be maintained at a constant level.

In acid base physiology, the Davenport diagram is a graphical tool, developed by Horace W. Davenport, that allows a clinician or investigator to describe blood bicarbonate concentrations and blood pH following a respiratory and/or metabolic acid-base disturbance. The diagram depicts a three-dimensional surface describing all possible states of chemical equilibria between gaseous carbon dioxide, aqueous bicarbonate and aqueous protons at the physiologically complex interface of the alveoli of the lungs and the alveolar capillaries. Although the surface represented in the diagram is experimentally determined, the Davenport diagram is rarely used in the clinical setting, but allows the investigator to envision the effects of physiological changes on blood acid-base chemistry. For clinical use there are two recent innovations: an Acid-Base Diagram which provides Text Descriptions for the abnormalities and a High Altitude Version that provides text descriptions appropriate for the altitude.

<span class="mw-page-title-main">Electrogenic sodium bicarbonate cotransporter 1</span> Protein-coding gene in the species Homo sapiens

Electrogenic sodium bicarbonate cotransporter 1, sodium bicarbonate cotransporter is a membrane transport protein that in humans is encoded by the SLC4A4 gene.

Sodium citrate may refer to any of the sodium salts of citric acid :

<span class="mw-page-title-main">Acid–base disorder</span> Medical condition

Acid–base imbalance is an abnormality of the human body's normal balance of acids and bases that causes the plasma pH to deviate out of the normal range. In the fetus, the normal range differs based on which umbilical vessel is sampled. It can exist in varying levels of severity, some life-threatening.

Krebs–Henseleit solution, developed by Hans Krebs and Kurt Henseleit, is a solution containing sodium (Na), potassium (K), chloride (Cl), calcium (Ca), magnesium sulfate (MgSO4), bicarbonate (HCO3), phosphate (PO4), glucose, and sometimes supplemented with albumin, and tromethamine (THAM).

<span class="mw-page-title-main">Intravenous sodium bicarbonate</span> Pharmaceutical drug

Intravenous sodium bicarbonate, also known as sodium hydrogen carbonate, is a medication primarily used to treat severe metabolic acidosis. For this purpose it is generally only used when the pH is less than 7.1 and when the underlying cause is either diarrhea, vomiting, or the kidneys. Other uses include high blood potassium, tricyclic antidepressant overdose, and cocaine toxicity as well as a number of other poisonings. It is given by injection into a vein.

References

  1. "Tromethamine". pubchem.ncbi.nlm.nih.gov.
  2. Gomori, G., Preparation of Buffers for Use in Enzyme Studies. Methods Enzymology., 1, 138-146 (1955).
  3. 1 2 FISCHER, Beda E.; HARING, Ulrich K.; TRIBOLET, Roger; SIGEL, Helmut (1979). "Metal Ion/Buffer Interactions. Stability of Binary and Ternary Complexes Containing 2-Amino-2(hydroxymethyl)-1,3-propanediol (Tris) and Adenosine 5'-Triphosphate (ATP)". European Journal of Biochemistry. 94 (2). Wiley: 523–530. doi: 10.1111/j.1432-1033.1979.tb12921.x . ISSN   0014-2956. PMID   428398.
  4. Stanley, David; Tunnicliffe, William (June 2008). "Management of life-threatening asthma in adults". Continuing Education in Anaesthesia, Critical Care & Pain. 8 (3): 95–99. doi: 10.1093/bjaceaccp/mkn012 . Retrieved 21 July 2017.
  5. Hoste, Eric A.; Colpaert, Kirsten; Vanholder, Raymond C.; Lameire, Norbert H.; De Waele, Jan J.; Blot, Stijn I.; Colardyn, Francis A. (May 2005). "Sodium bicarbonate versus THAM in ICU patients with mild metabolic acidosis". Journal of Nephrology. 18 (3): 303–307. ISSN   1121-8428. PMID   16013019.
  6. BNF 73 March-September 2017. British Medical Association,, Royal Pharmaceutical Society of Great Britain. London. 21 March 2017. ISBN   978-0857112767. OCLC   988086079.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
  7. Holert, Johannes; Borker, Aron; Nübel, Laura Lucia; Daniel, Rolf; Poehlein, Anja; Philipp, Bodo (8 January 2024). "Bacteria use a catabolic patchwork pathway of apparently recent origin for degradation of the synthetic buffer compound TRIS". The ISME Journal. 18 (1): wrad023. doi:10.1093/ismejo/wrad023. ISSN   1751-7362.
  8. 1 2 "Sigma tris(hydroxymethyl)aminomethane; Tris Technical Bulletin No. 106B" (PDF). Sigma-Aldrich. Retrieved 4 June 2020.
  9. 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.
  10. Ghalanbor, Z; et al. (2008). "Binding of tris to Bacillus licheniformis alpha-amylase can affect its starch hydrolysis activity". Protein Pept. Lett. 15 (2): 212–214. doi:10.2174/092986608783489616. PMID   18289113.
  11. Markofsky, Sheldon, B. (15 October 2011). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Vol. 24. p. 296. doi:10.1002/14356007.a17_401.pub2. ISBN   978-3527306732.{{cite book}}: CS1 maint: multiple names: authors list (link)
  12. Irvin, R.T.; MacAlister, T.J.; Costerton, J.W. (1981). "Tris(hydroxymethyl)aminomethane Buffer Modification of Escherichia coli Outer Membrane Permeability". J. Bacteriol. 145 (3): 1397–1403. doi:10.1128/JB.145.3.1397-1403.1981. PMC   217144 . PMID   7009585.
  13. Factsheet modernatx.com
  14. Vaccines and Related Biological Products Advisory Committee Meeting October 26, 2021 fda.gov
  15. 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. doi:10.1164/ajrccm.161.4.9906031. PMID   10764304.
  16. Hoste, EA; Colpaert, K; Vanholder, RC; Lameire, NH; De Waele, JJ; Blot, SI; Colardyn, FA (2005). "Sodium bicarbonate versus THAM in ICU patients with mild metabolic acidosis". Journal of Nephrology. 18 (3): 303–7. PMID   16013019.