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'''Tris''', or '''tris(hydroxymethyl)aminomethane''', or known during medical use as '''tromethamine''' or '''THAM''', is an [[organic compound]] with the formula (HOCH<sub>2</sub>)<sub>3</sub>CNH<sub>2</sub>. It is extensively used in [[biochemistry]] and [[molecular biology]] as a component of [[buffer solution]]s<ref>Gomori, G., [http://2008.igem.org/wiki/images/8/84/Protein_Buffers.pdf Preparation of Buffers for Use in Enzyme Studies]. Methods Enzymology., 1, 138-146 (1955).</ref> such as in [[TAE buffer|TAE]] and [[TBE buffer]]s, especially for solutions of [[nucleic acid]]s. 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.<ref name="metalions">{{cite journal | last1=FISCHER | first1=Beda E. | last2=HARING | first2=Ulrich K. | last3=TRIBOLET | first3=Roger | last4=SIGEL | first4=Helmut | title=Metal Ion/Buffer Interactions. Stability of Binary and Ternary Complexes Containing 2-Amino-2(hydroxymethyl)-1,3-propanediol (Tris) and Adenosine 5'-Triphosphate (ATP) | journal=European Journal of Biochemistry | publisher=Wiley | volume=94 | issue=2 | year=1979 | issn=0014-2956 | doi=10.1111/j.1432-1033.1979.tb12921.x | pages=523–530| pmid=428398 | doi-access=free }}</ref> 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.<ref>{{cite journal|last1=Stanley|first1=David|last2=Tunnicliffe|first2=William|title=Management of life-threatening asthma in adults|journal=Continuing Education in Anaesthesia, Critical Care & Pain|date=June 2008|volume=8|issue=3|pages=95–99|doi=10.1093/bjaceaccp/mkn012|url=https://academic.oup.com/bjaed/article/8/3/95/293339/Management-of-life-threatening-asthma-in-adults|access-date=21 July 2017|doi-access=free}}</ref><ref>{{Cite journal|last1=Hoste|first1=Eric A.|last2=Colpaert|first2=Kirsten|last3=Vanholder|first3=Raymond C.|last4=Lameire|first4=Norbert H.|last5=De Waele|first5=Jan J.|last6=Blot|first6=Stijn I.|last7=Colardyn|first7=Francis A.|date=May 2005|title=Sodium bicarbonate versus THAM in ICU patients with mild metabolic acidosis|journal=Journal of Nephrology|volume=18|issue=3|pages=303–307|issn=1121-8428|pmid=16013019}}</ref> Some medications are formulated as the "tromethamine salt" including [[Hemabate]] ([[carboprost]] as trometamol salt), and "[[ketorolac]] trometamol".<ref>{{Cite book|title=BNF 73 March-September 2017|others=British Medical Association,, Royal Pharmaceutical Society of Great Britain|date=21 March 2017|isbn=978-0857112767|location=London|oclc=988086079}}</ref> In 2023 a strain of ''[[Pseudomonas]] hunanensis'' was found to be able to degrade TRIS buffer.<ref>{{Cite journal| doi = 10.1093/ismejo/wrad023| issn = 1751-7362| volume = 18| issue = 1| pages = wrad023| last1 = Holert| first1 = Johannes| last2 = Borker| first2 = Aron| last3 = Nübel| first3 = Laura Lucia| last4 = Daniel| first4 = Rolf| last5 = Poehlein| first5 = Anja| last6 = Philipp| first6 = Bodo| title = Bacteria use a catabolic patchwork pathway of apparently recent origin for degradation of the synthetic buffer compound TRIS| journal = The ISME Journal| date = 2024-01-08| url = https://academic.oup.com/ismej/article/doi/10.1093/ismejo/wrad023/7513125}}</ref>
'''Tris''', or '''tris(hydroxymethyl)aminomethane''', or known during medical use as '''tromethamine''' or '''THAM''', is an [[organic compound]] with the formula (HOCH<sub>2</sub>)<sub>3</sub>CNH<sub>2</sub>. It is extensively used in [[biochemistry]] and [[molecular biology]] as a component of [[buffer solution]]s<ref>Gomori, G., [http://2008.igem.org/wiki/images/8/84/Protein_Buffers.pdf Preparation of Buffers for Use in Enzyme Studies]. Methods Enzymology., 1, 138-146 (1955).</ref> such as in [[TAE buffer|TAE]] and [[TBE buffer]]s, especially for solutions of [[nucleic acid]]s. 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.<ref name="metalions">{{cite journal | last1=FISCHER | first1=Beda E. | last2=HARING | first2=Ulrich K. | last3=TRIBOLET | first3=Roger | last4=SIGEL | first4=Helmut | title=Metal Ion/Buffer Interactions. Stability of Binary and Ternary Complexes Containing 2-Amino-2(hydroxymethyl)-1,3-propanediol (Tris) and Adenosine 5'-Triphosphate (ATP) | journal=European Journal of Biochemistry | publisher=Wiley | volume=94 | issue=2 | year=1979 | issn=0014-2956 | doi=10.1111/j.1432-1033.1979.tb12921.x | pages=523–530| pmid=428398 | doi-access=free }}</ref> In medicine, tris (known as 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.<ref>{{cite journal|last1=Stanley|first1=David|last2=Tunnicliffe|first2=William|title=Management of life-threatening asthma in adults|journal=Continuing Education in Anaesthesia, Critical Care & Pain|date=June 2008|volume=8|issue=3|pages=95–99|doi=10.1093/bjaceaccp/mkn012|url=https://academic.oup.com/bjaed/article/8/3/95/293339/Management-of-life-threatening-asthma-in-adults|access-date=21 July 2017|doi-access=free|url-access=subscription}}</ref><ref>{{Cite journal|last1=Hoste|first1=Eric A.|last2=Colpaert|first2=Kirsten|last3=Vanholder|first3=Raymond C.|last4=Lameire|first4=Norbert H.|last5=De Waele|first5=Jan J.|last6=Blot|first6=Stijn I.|last7=Colardyn|first7=Francis A.|date=May 2005|title=Sodium bicarbonate versus THAM in ICU patients with mild metabolic acidosis|journal=Journal of Nephrology|volume=18|issue=3|pages=303–307|issn=1121-8428|pmid=16013019}}</ref> Some medications are formulated as the "tromethamine salt" including [[Hemabate]] ([[carboprost]] as trometamol salt), and "[[ketorolac]] trometamol".<ref>{{Cite book|title=BNF 73 March-September 2017|others=British Medical Association,, Royal Pharmaceutical Society of Great Britain|date=21 March 2017|isbn=978-0-85711-276-7|location=London|oclc=988086079}}</ref> In 2023 a strain of ''[[Pseudomonas]] hunanensis'' was found to be able to degrade TRIS buffer.<ref>{{Cite journal| doi = 10.1093/ismejo/wrad023| issn = 1751-7362| volume = 18| issue = 1| article-number = wrad023| last1 = Holert| first1 = Johannes| last2 = Borker| first2 = Aron| last3 = Nübel| first3 = Laura Lucia| last4 = Daniel| first4 = Rolf| last5 = Poehlein| first5 = Anja| last6 = Philipp| first6 = Bodo| title = Bacteria use a catabolic patchwork pathway of apparently recent origin for degradation of the synthetic buffer compound TRIS| journal = The ISME Journal| date = 2024-01-08| url = https://academic.oup.com/ismej/article/doi/10.1093/ismejo/wrad023/7513125| pmc = 10848231}}</ref>


Since Tris' pKa is more strongly temperature dependent, its use is not recommended in biochemical applications requiring consistent pH over a range of temperatures. Moreover, the temperature dependance of the pKa (and in turn buffer solution pH) makes pH adjustment difficult.<ref>{{cite journal |last1=Stoll |first1=Vincent S. |last2=Blanchard |first2=John S. |title=[4] Buffers: Principles and practice |journal=Methods in Enzymology |date=1 January 1990 |volume=182 |pages=24–38 |doi=10.1016/0076-6879(90)82006-N}}</ref> (E.g., the 'room temperature' pH adjustment would not translate to 'measurement conditions' pH, unless care is taken to calculate the effect of temperature, see below.)
Since Tris' pKa is more strongly temperature dependent, its use is not recommended in biochemical applications requiring consistent pH over a range of temperatures. Moreover, the temperature dependence of the pKa (and in turn buffer solution pH) makes pH adjustment difficult.<ref>{{cite journal |last1=Stoll |first1=Vincent S. |last2=Blanchard |first2=John S. |title=[4] Buffers: Principles and practice |journal=Methods in Enzymology |date=1 January 1990 |volume=182 |pages=24–38 |doi=10.1016/0076-6879(90)82006-N}}</ref> (E.g., the 'room temperature' pH adjustment would not translate to 'measurement conditions' pH, unless care is taken to calculate the effect of temperature, see below.)


==Buffering features==
==Buffering features==
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==Preparation==
==Preparation==
Tris is prepared industrially by the exhaustive condensation of [[nitromethane]] with [[formaldehyde]] under basic conditions (i.e. repeated [[Henry reaction]]s) to produce the intermediate (HOCH<sub>2</sub>)<sub>3</sub>CNO<sub>2</sub>, which is subsequently [[hydrogenation|hydrogenated]] to give the final product.<ref>{{Cite book|last1=Markofsky|first1=Sheldon, B.|chapter=Nitro Compounds, Aliphatic|title=Ullmann's Encyclopedia of Industrial Chemistry|date=15 October 2011|volume=24|page=296|doi=10.1002/14356007.a17_401.pub2|isbn=978-3527306732}}</ref>
Tris is prepared industrially by the exhaustive condensation of [[nitromethane]] with [[formaldehyde]] under basic conditions (i.e. repeated [[Henry reaction]]s) to produce the intermediate (HOCH<sub>2</sub>)<sub>3</sub>CNO<sub>2</sub>, which is subsequently [[hydrogenation|hydrogenated]] to give the final product.<ref>{{Cite book|last1=Markofsky|first1=Sheldon, B.|chapter=Nitro Compounds, Aliphatic|title=Ullmann's Encyclopedia of Industrial Chemistry|date=15 October 2011|volume=24|page=296|doi=10.1002/14356007.a17_401.pub2|isbn=978-3-527-30673-2}}</ref>


==Uses==
==Uses==

Latest revision as of 05:33, 4 October 2025

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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[1] 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.[2] In medicine, tris (known as 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.[3][4] Some medications are formulated as the "tromethamine salt" including Hemabate (carboprost as trometamol salt), and "ketorolac trometamol".[5] In 2023 a strain of Pseudomonas hunanensis was found to be able to degrade TRIS buffer.[6]

Since Tris' pKa is more strongly temperature dependent, its use is not recommended in biochemical applications requiring consistent pH over a range of temperatures. Moreover, the temperature dependence of the pKa (and in turn buffer solution pH) makes pH adjustment difficult.[7] (E.g., the 'room temperature' pH adjustment would not translate to 'measurement conditions' pH, unless care is taken to calculate the effect of temperature, see below.)

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

  • In general, as temperature decreases from 25 °C to 5 °C the pH of a tris buffer will increase an average of 0.03 units per degree. As temperature rises from 25 °C to 37 °C, the pH of a tris buffer will decrease an average of 0.025 units per degree.[8]
  • In general, a 10-fold increase in tris buffer concentration will lead to a 0.05 unit increase in pH and vice versa.[8]
  • Silver-containing single-junction pH electrodes (e.g., silver chloride electrodes) are incompatible with tris since an Ag-tris precipitate forms which clogs the junction. Double-junction electrodes are resistant to this problem, and non-silver containing electrodes are immune.

Buffer inhibition

  • Tris inhibits a number of enzymes,[9][10] and therefore should be used with care when studying proteins.
  • Tris can also inhibit enzyme activity via chelation of metal ions.[2]

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

References

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  1. ↑ Gomori, G., Preparation of Buffers for Use in Enzyme Studies. Methods Enzymology., 1, 138-146 (1955).
  2. ↑ a b Script error: No such module "Citation/CS1".
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  8. ↑ a b Script error: No such module "citation/CS1".
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  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ Factsheet modernatx.com
  14. ↑ Vaccines and Related Biological Products Advisory Committee Meeting October 26, 2021 fda.gov
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ Script error: No such module "Citation/CS1".

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