Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tris: Difference between pages

{{about|the chemical widely used as a biochemical buffer}}

{{Use dmy dates|date=May 2024}}

| Watchedfields = changed

| verifiedrevid = 470617284

| ImageFile = 2-amino-2-(hydroxymethyl)propane-1,3-diol 200.svg

| PIN = 2-Amino-2-(hydroxymethyl)propane-1,3-diol

| OtherNames = TRIS, Tris, Tris base, Tris buffer, Trizma, Trisamine, THAM, Tromethamine, Trometamol, Tromethane, Trisaminol, Tris(hydroxymethyl)aminomethane

|Section1={{Chembox Identifiers

| CASNo = 77-86-1

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo_Comment = (free base)

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 1185-53-1

| CASNo2_Comment = (hydrochloride)

| CASNo3_Ref = {{cascite|correct|CAS}}

| CASNo3 = 6850-28-8

| CASNo3_Comment = (acetate salt)

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1200391

| DrugBank = DB03754

| EC_number = 201-064-4

| IUPHAR_ligand = 7328

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00396

| RTECS = TY2900000

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 383V75M34E

| UNII2_Comment = (hydrochloride)

| SMILES = OCC(N)(CO)CO

|Section2={{Chembox Properties

| C=4 | H=11 | N=1 | O=3

| Density = 1.328g/cm³

| Solubility = ~50 g/100 mL (25 °C)

| MeltingPt = >175-176 °C (448-449 K)

| BoilingPtC = 219

| pKa = 8.07 (conjugate acid)

|Section6={{Chembox Pharmacology

| ATCCode_prefix = B05

| ATCCode_suffix = BB03

| ATC_Supplemental = {{ATC|B05|XX02}}

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/t7111.htm External MSDS]

| Hazards_ref=<ref>{{cite web |title=Tromethamine |url=https://pubchem.ncbi.nlm.nih.gov/compound/6503#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|332+313|362|403+233|405}}

'''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 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>

==Buffering features==

The [[conjugate acid]] of tris has a [[Acid dissociation constant|p''K''_a]] of 8.07 at 25&nbsp;°C, which implies that the buffer has an effective [[pH]] range between 7.1 and 9.1 (p''K''_a ± 1) at room temperature.

===Buffer details===

*In general, as temperature decreases from 25&nbsp;°C to 5&nbsp;°C the pH of a tris buffer will increase an average of 0.03 units per degree. As temperature rises from 25&nbsp;°C to 37&nbsp;°C, the pH of a tris buffer will decrease an average of 0.025 units per degree.<ref name="Sigma Technical bulletin 106b">{{cite web | title=Sigma tris(hydroxymethyl)aminomethane; Tris Technical Bulletin No. 106B | website=Sigma-Aldrich | url=https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Bulletin/1/106bbul.pdf | access-date=2020-06-04}}</ref>

*In general, a 10-fold increase in tris buffer concentration will lead to a 0.05 unit increase in pH and vice versa.<ref name="Sigma Technical bulletin 106b"/>

*[[Silver]]-containing single-junction pH electrodes (e.g., [[silver chloride electrode]]s) 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,<ref name="D">{{cite journal|last= Desmarais|first=WT|title=The 1.20 Å resolution crystal structure of the aminopeptidase from Aeromonas proteolytica complexed with tris: A tale of buffer inhibition|journal= Structure|volume=10|issue=8|pages=1063–1072|year=2002|pmid= 12176384|doi= 10.1016/S0969-2126(02)00810-9|display-authors=etal|doi-access=free}}</ref><ref name="g">{{cite journal|last=Ghalanbor|first=Z|title=Binding of tris to Bacillus licheniformis alpha-amylase can affect its starch hydrolysis activity|journal=Protein Pept. Lett.|volume=15|issue=2|pages=212–214|year=2008|pmid= 18289113|doi=10.2174/092986608783489616|display-authors=etal}}</ref> and therefore should be used with care when studying proteins.

*Tris can also inhibit enzyme activity via [[chelation]] of metal ions.<ref name="metalions"/>

==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 (HOCH₂)₃CNO₂, 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>

==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.<ref>{{cite journal| title=Tris(hydroxymethyl)aminomethane Buffer Modification of ''Escherichia coli'' Outer Membrane Permeability |last1=Irvin |first1=R.T. |last2=MacAlister |first2=T.J. |last3=Costerton |first3=J.W. |journal=[[J. Bacteriol.]] |year=1981 |volume=145 |issue=3 |pages=1397–1403|doi=10.1128/JB.145.3.1397-1403.1981 |pmid=7009585 |pmc=217144 }}</ref> It is a component of the [[Moderna COVID-19 vaccine]]<ref>[https://www.modernatx.com/covid19vaccine-eua/eua-fact-sheet-recipients.pdf Factsheet] modernatx.com</ref> and the [[Pfizer–BioNTech COVID-19 vaccine|Pfizer-BioNTech COVID-19 vaccine]] for use in children 5 through 11 years of age.<ref>[https://www.fda.gov/media/153447/download Vaccines and Related Biological Products Advisory Committee Meeting October 26, 2021] fda.gov</ref>

===Medical===

Tris (usually known as THAM in this context) is used as alternative to [[sodium bicarbonate]] in the treatment of [[metabolic acidosis]].<ref name="Kallet">{{cite journal|last=Kallet|first=RH |author2=Jasmer RM |author3=Luce JM|title=The treatment of acidosis in acute lung injury with tris-hydroxymethyl aminomethane (THAM)|journal=American Journal of Respiratory and Critical Care Medicine|volume=161|issue=4|pages=1149–1153|year=2000|pmid=10764304|doi=10.1164/ajrccm.161.4.9906031|display-authors=etal}}</ref><ref>{{cite journal|last1=Hoste|first1=EA|last2=Colpaert|first2=K|last3=Vanholder|first3=RC|last4=Lameire|first4=NH|last5=De Waele|first5=JJ|last6=Blot|first6=SI|last7=Colardyn|first7=FA|title=Sodium bicarbonate versus THAM in ICU patients with mild metabolic acidosis|journal=Journal of Nephrology|date=2005|volume=18|issue=3|pages=303–7|pmid=16013019}}</ref>

==See also==

*[[MOPS]]

*[[HEPES]]

*[[MES (buffer)|MES]]

*[[Buffer solution#Common buffer compounds used in biology|Common buffer compounds used in biology]]

==References==

{{reflist|2}}

[[Category:Polyols]]

[[Category:Amines]]

[[Category:Buffer solutions]]