Tris

Last updated
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]

Contents

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

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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 (2024-01-08). "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 2020-06-04.
  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. https://www.modernatx.com/covid19vaccine-eua/eua-fact-sheet-recipients.pdf [ bare URL PDF ]
  14. https://www.fda.gov/media/153447/download [ bare URL PDF ]
  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.