Trimethylamine

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Template:Chembox ECNumberTemplate:Chembox E numberTemplate:Chembox SolubilityInWater
Trimethylamine[1]
IUPAC name Trimethylamine
Other names N,N-Dimethylmethanamine
Identifiers
3D model (JSmol)
Abbreviations TMA
NMe3
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Properties
C3H9N
Molar mass 59.11 g/mol
Appearance Clear colorless liquid
Density 0.67 g/ml (0 °C)
Melting point
Boiling point
Basicity (pKb) 4.13
Hazards
R-phrases R12 R20/22 R34
S-phrases (S1/2) S3 S16 S26 S29 S36/37/39 S45
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Trimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia-like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 °C and is a gas at room temperature. Trimethylamine usually comes in pressurized gas cylinders or as a 40% solution in water. Trimethylamine is a nitrogenous base and its positively charged cation is called trimethylammonium cation. A common salt of trimethylamine is trimethylammonium chloride, a hygroscopic colorless solid.

Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the fishy odor often associated with fouling fish, bacterial vagina infections, and bad breath. It is also associated with taking large doses of choline and carnitine.

Applications

Trimethylamine is used in the chemical synthesis of choline, tetramethylammonium hydroxide, plant growth regulators, strongly basic anion exchange resins, and dye leveling agents. Its fish-like odor has proven useful in applications such as the creation of gas sensors to test for fish freshness.

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 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.

See also

References

  1. Merck Index<link rel="stylesheet" type="text/css" href="http://en.wikipedia.org/w/index.php?title=User:Lupin/navpop.css&action=raw&ctype=text/css&dontcountme=s">, 11th Edition, 9625.

External links

de:Trimethylamin nl:Trimethylamine


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