Trimethylamine

Trimethylamine

Identifiers
CAS Number	75-50-3 Y
3DMet	B00133
Beilstein Reference	956566
ChEBI	CHEBI:18139 Y
ChEMBL	ChEMBL439723 Y
ChemSpider	1114 Y
EC Number	200-875-0
Jmol 3D model	Interactive image
KEGG	C00565 N
PubChem	1146
RTECS number	PA0350000
UNII	LHH7G8O305 Y
UN number	1083
InChI InChI=1S/C3H9N/c1-4(2)3/h1-3H3 Y Key: GETQZCLCWQTVFV-UHFFFAOYSA-N Y
SMILES CN(C)C
Properties
Chemical formula	C3H9N
Molar mass	59.11 g·mol−1
Appearance	Colorless gas
Odor	Fishy, ammoniacal
Density	670 kg m−3 (at 0 °C) 627.0 kg m−3 (at 25 °C)
Melting point	−117.20 °C; −178.96 °F; 155.95 K
Boiling point	3 to 7 °C; 37 to 44 °F; 276 to 280 K
Solubility in water	Miscible
log P	0.119
Vapor pressure	188.7 kPa (at 20 °C)
Henry's law constant (kH)	95 μmol Pa−1 kg−1
Basicity (pKb)	4.19
Thermochemistry
Std enthalpy of formation (ΔfHo298)	−24.5 to −23.0 kJ mol−1
Vapor pressure	{{{value}}}
Related compounds
Related amines	Dimethylamine N-Nitrosodimethylamine Diethylamine Triethylamine Diisopropylamine Dimethylaminopropylamine Diethylenetriamine N,N-Diisopropylethylamine Triisopropylamine Tris(2-aminoethyl)amine Mechlorethamine HN1 (nitrogen mustard) HN3 (nitrogen mustard)
Related compounds	Unsymmetrical dimethylhydrazine Biguanide Dithiobiuret
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Trimethylamine is an organic compound with the formula N(CH₃)₃. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations. It is a gas at room temperature but is usually sold in pressurized gas cylinders or as a 40% solution in water.

Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the odor often associated with rotting fish, some infections, bad breath and can be a cause of vaginal odor due to bacterial vaginosis. It is also associated with taking large doses of choline and carnitine.

Trimethylamine is a nitrogenous base and can be readily protonated to give trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications.

Production

Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:

3 CH₃OH + NH₃ → (CH₃)₃N + 3 H₂O

This reaction coproduces the other methylamines, dimethylamine (CH₃)₂NH and methylamine CH₃NH₂.

Trimethylamine has also been prepared via a reaction of ammonium chloride and paraformaldehyde, according to the following equation:

9 (CH₂=O)_n + 2n NH₄Cl → 2n (CH₃)₃N•HCl + 3n H₂O + 3n CO₂↑

Applications

Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators or herbicides, strongly basic anion exchange resins, dye leveling agents and a number of basic dyes. Gas sensors to test for fish freshness detect trimethylamine.

Trimethylaminuria

Main article: Trimethylaminuria

Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. A condition similar to trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell, especially after eating food containing a high proportion of rapeseed.

See also

• Ammonia, NH₃
• Ammonium, NH₄⁺
• Methylamine, (CH₃)NH₂
• Triethylamine (TEA)

External links

• Molecule of the Month: Trimethylamine
• NIST Webbook data
• CDC - NIOSH Pocket Guide to Chemical Hazards