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Information about Trimethylamine



Trimethylamine[1]
IUPAC nameTrimethylamine
Other namesN,N-Dimethylmethanamine
Identifiers
AbbreviationsTMA
NMe3
CAS number75-50-3
PubChem1146
EINECS number200-875-0
SMILESCN(C)C
InChIInChI=1/C3H8N/c1-4(2)3/h1H2,2-3H3
Properties
Molecular formulaC3H9N
Molar mass59.11 g/mol
AppearanceClear colorless liquid
Density0.67 g/ml (0 °C)
Melting point -117.08 C, 0 K, 0 F
Boiling point 2.87 C, 0 K, 0 F
Solubility in waterMiscible
Basicity (pKb)4.13
Hazards
NFPA 704
4
2
0
 
R-phrasesR12 R20/22 R34
S-phrasesS1/2 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)


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, 11th Edition, 9625.

External links

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
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The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981.
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smiles

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Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. According to the Brønsted-Lowry theory of acids and bases an acid is only recognised by its reaction with a base.
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NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. It defines the colloquial "fire diamond" used by emergency personnel to quickly and easily identify the risks posed by nearby hazardous materials.
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R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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Hygroscopy is the ability of a substance to attract water molecules from the surrounding environment through either absorption or adsorption.

Hygroscopic substances include honey, glycerin, ethanol, methanol, concentrated sulfuric acid, methamphetamine, and concentrated
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Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. Structurally amines resemble ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups.
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odor or odour (see spelling differences) is a volatilized chemical compound, generally at a very low concentration, which humans and other animals perceive by the sense of olfaction. Odors are also called smells, which can refer to both pleasant and unpleasant odors.
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Ammonia is a compound with the formula NH3. It is normally encountered as a gas with a characteristic pungent odor. Ammonia contributes significantly to the nutritional needs of the planet as a precursor to foodstuffs and fertilizers.
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Gas cylinder or tank is a pressure vessel used to store gases at high pressure.

Applications

Applications for gas cylinders include:
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Nitrogenous bases are organic compounds that owe their basic properties to the lone pair of electrons of a nitrogen atom. Typical nitrogenous bases are ammonia (NH3), triethylamine, pyridine, and the nucleobases adenine, guanine, thymine, cytosine, and uracil.
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