Trimethylamine

Trimethylamine
IUPAC name Trimethylamine[citation needed]
Other names N,N-Dimethylmethanamine[citation needed]
Identifiers
Abbreviations	TMA[citation needed]
CAS number	75-50-3 Y
PubChem	1146
ChemSpider	1114 Y
UNII	LHH7G8O305 Y
EC number	200-875-0
UN number	1083
KEGG	C00565 Y
ChEBI	CHEBI:18139 Y
ChEMBL	CHEMBL439723 Y
RTECS number	PA0350000
Beilstein Reference	956566
3DMet	B00133
Jmol-3D images	Image 1
SMILES CN(C)C
InChI InChI=1S/C3H9N/c1-4(2)3/h1-3H3 Y Key: GETQZCLCWQTVFV-UHFFFAOYSA-N Y
Properties
Molecular formula	C3H9N
Molar mass	59.11 g mol−1
Exact mass	59.073499293 g mol−1
Appearance	Colorless, transparent gas
Odor	Ichtyal, ammoniacal
Density	670 mg cm−1 (at 0 °C)
Melting point	-117 °C, 155.95 K, -179 °F
Boiling point	-3 °C, 270 K, 26 °F
Solubility in water	Miscible
log P	0.119
Vapor pressure	91.74 kPa (at 21 °C)
Thermochemistry
Std enthalpy of formation ΔfHo298	−24.5–−23.0 kJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H220, H315, H318, H332, H335
GHS precautionary statements	P210, P261, P280, P305+351+338
EU Index	612-001-00-9
EU classification	F+ Xn
R-phrases	R12, R20, R37/38, R41
S-phrases	(S2), S16, S26, S29
NFPA 704	4 2 0
Flash point	−7 °C
Autoignition temperature	190 °C
Explosive limits	2–11.6%
LD50	500 mg kg−1 (oral, rat) 19 g m−3 (inhalation, mouse)
Related compounds
Related compounds	Triethylamine
Y (verify) (what is: Y/N?) 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.

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, 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.^{[citation needed]}

See also

• Ammonia, NH₃
• Ammonium, NH₄⁺
• Methylamine (CH₃)NH₂
• Dimethylamine (CH₃)₂NH
• Triethylamine (TEA)

External links

• Molecule of the Month: Trimethylamine
• NIST Webbook data