Trimethylamine[1]
IUPAC name	Trimethylamine
Other names	N,N-Dimethylmethanamine
Identifiers
Abbreviations	TMA, NMe3
CAS number	75-50-3 Y
PubChem	1146
EC number	200-875-0
RTECS number	1.1.78 – 31.1.87
SMILES	CN(C)C
InChI	1/C3H8N/c1-4(2)3/h1H2,2-3H3
ChemSpider ID	1114
Properties
Molecular formula	C3H9N
Molar mass	59.11 g/mol
Appearance	Colourless gas
Density	0.67 g/mL (0 °C)
Melting point	-117.08 °C, 156 K, -179 °F
Boiling point	2.87 °C, 276 K, 37 °F
Solubility in water	Miscible
Basicity (pKb)	4.13
Hazards
R-phrases	R12 R20/22 R34
S-phrases	(S1/2) S3 S16 S26 S29 S36/37/39 S45
NFPA 704	4 2 0
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 fouling fish, some infections, and bad breath. 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.

Contents 1 Production 2 Applications 3 Trimethylaminuria 4 See also 5 References 6 External links

[edit] Production

Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:^[2]

3 CH₃OH + NH₃ → (CH₃)₃N + 3 H₂O

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

Trimethylamine has also been prepared via a reaction of ammonium chloride and paraformaldehyde,^[3] according to the following equation:

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

[edit] Applications

Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators, strongly basic anion exchange resins, and dye leveling agents.^[2] Gas sensors to test for fish freshness detect trimethylamine.

[edit] 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 trimethylaminuria-like condition 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.

[edit] See also

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

[edit] References

[edit] External links

• Molecule of the Month: Trimethylamine
• NIST Webbook data