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tromethamine

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tromethamine

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Also known as tris, trometamol, 2-Amino-2-(hydroxymethyl)-1,3-propanediol, Tris base, Tris-base, Tris amino, Tris buffer, 1,1,1-tris(hydroxymethyl)methanamine

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 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. In medicine, tris (known as tromethamine) is occasionally used as a drug, given in intensive care for

Chemical data

Formula
C4H11NO3
Molecular weight
121.14 g/mol
IUPAC name
2-amino-2-(hydroxymethyl)propane-1,3-diol
SMILES
C(C(CO)(CO)N)O
InChIKey
LENZDBCJOHFCAS-UHFFFAOYSA-N
XLogP
-2.9
Polar surface area
86.7 Ų
H-bond donors
4
H-bond acceptors
4
Formal charge
0

via PubChem

~4 min read

Encyclopedic overview

8 sections
Contents
  • Buffering features
  • Buffer details
  • Buffer inhibition
  • Preparation
  • Uses
  • Medical
  • See also
  • References

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 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. 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. Some medications are formulated as the "tromethamine salt" including Hemabate (carboprost as trometamol salt), and "ketorolac trometamol". In 2023 a strain of Pseudomonas hunanensis was found to be able to degrade TRIS buffer.

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. (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.)

Excerpted from Wikipedia’s “tromethamine” article, available under the CC BY-SA 4.0 licence.