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Tetramethylammonium
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Tetramethylammonium
Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula [Me4N]+ and consists of four methyl groups (−CH3, denoted Me) attached to a central nitrogen atom. The cation is isoelectronic with neopentane (Me4C). It is positively-charged and can only be isolated in association with a counter-ion. Common salts include tetramethylammonium chloride and tetramethylammonium hydroxide. Tetramethylammonium salts are used in chemical synthesis and in pharmacological research. It confers no color to its salts.
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). TMA also occurs within the crystal structure Tsaregorodtsevite, a rare Sodalite group mineral with the formula N(CH3)4AlSi5O12 found on Gora Yaruta Mountain, Khanty-Mansi Autonomous Okrug, Russia.
Tetramethylammonium ion is typically prepared by the reaction between trimethylamine and a methyl chloride:
[14C]-labeled TMA has been made by this method.
Although this reaction is suitable for the common halides, tetramethylammonium salts with more complex anions may be prepared by salt metathesis reactions, e.g. tetramethylammonium borohydride has been made from tetramethylammonium hydroxide as shown:
Although TMA salts do possess some of the phase-transfer catalytic properties that are characteristic of quaternary ammonium compounds, they tend to behave atypically because of the relatively high hydrophilicity of the TMA cation.
TMA cation is hydrophilic. The octanol-water partition coefficient of TMA iodide, Po-w, is 1.2×10−4 (or log P ≈ −3.92).
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Tetramethylammonium
Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula [Me4N]+ and consists of four methyl groups (−CH3, denoted Me) attached to a central nitrogen atom. The cation is isoelectronic with neopentane (Me4C). It is positively-charged and can only be isolated in association with a counter-ion. Common salts include tetramethylammonium chloride and tetramethylammonium hydroxide. Tetramethylammonium salts are used in chemical synthesis and in pharmacological research. It confers no color to its salts.
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). TMA also occurs within the crystal structure Tsaregorodtsevite, a rare Sodalite group mineral with the formula N(CH3)4AlSi5O12 found on Gora Yaruta Mountain, Khanty-Mansi Autonomous Okrug, Russia.
Tetramethylammonium ion is typically prepared by the reaction between trimethylamine and a methyl chloride:
[14C]-labeled TMA has been made by this method.
Although this reaction is suitable for the common halides, tetramethylammonium salts with more complex anions may be prepared by salt metathesis reactions, e.g. tetramethylammonium borohydride has been made from tetramethylammonium hydroxide as shown:
Although TMA salts do possess some of the phase-transfer catalytic properties that are characteristic of quaternary ammonium compounds, they tend to behave atypically because of the relatively high hydrophilicity of the TMA cation.
TMA cation is hydrophilic. The octanol-water partition coefficient of TMA iodide, Po-w, is 1.2×10−4 (or log P ≈ −3.92).
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