Tetramethylammonium
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Preferred IUPAC name
N,N,N-Trimethylmethanaminium
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| Other names
Tetramethylammonium
Tetramethylazanium Tetramine |
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3D model (Jmol)
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PubChem CID
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| Properties | |
| C4H12N+ | |
| Molar mass | 74.14 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Tetramethylammonium (TMA) or (Me4N+) is the simplest quaternary ammonium cation consisting of four methyl groups attached to a central nitrogen atom, and is isoelectronic with neopentane. It is positively charged and must exist in association with a counter-ion, and is most commonly found in simple salts such as tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide and tetramethylammonium hydroxide, and can also form the unusual auride. Tetramethylammonium salts are used in chemical synthesis and are widely employed in pharmacological research. They also occur as toxic natural products, although the counterions may be difficult to identify. The identity of the anion associated with the tetramethylammonium cation frequently has little or no bearing on a particular chemical or biological type of action, but this is not invariably so.
In the toxicological literature, naturally occurring tetramethylammonium (anion unspecified) is often referred to by the name "tetramine". Unfortunately, this non-systematic or "trivial" name is also used for other chemical entities, including a toxic rodenticide (Tetramethylenedisulfotetramine). Similarly, the acronym "TMA", which is frequently used for tetramethylammonium in the pharmacological literature, may also refer to the investigational drug 3,4,5-trimethoxyamphetamine, which, being a close structural analog of mescaline, has been the subject of numerous publications.
TMA has been detected in or isolated from a number of marine organisms, mostly amongst the Cnidaria and Mollusca, notably in some species of Neptunea (commonly called whelks) that are eaten by humans. It has also been found in one plant, the African Courbonia virgata (Cappariaceae).
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