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tetramethylammonium

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EntityQ153485· pop 10· linked from 32 articles

tetramethylammonium

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Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula and consists of four methyl groups (, denoted Me) attached to a central nitrogen atom. The cation is isoelectronic with neopentane (). 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.

Chemical data

Formula
C4H12N+
Molecular weight
74.14 g/mol
IUPAC name
tetramethylazanium
SMILES
C[N+](C)(C)C
InChIKey
QEMXHQIAXOOASZ-UHFFFAOYSA-N
XLogP
0.3
Polar surface area
0 Ų
H-bond donors
0
H-bond acceptors
0
Formal charge
1

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Has part
nitrogen
Mass
74.097
Show 4 more facts
canonical SMILES
C[N+](C)(C)C
found in taxon
Maerua subcordata
Commons category
Tetramethylammonium cation
chemical formula
C₄H₁₂N⁺
Sources (4)

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Encyclopedic overview

9 sections
Contents
  • Common nomenclature
  • Occurrence
  • Preparation, reactions, solution properties
  • Pharmacology
  • Absorption; distribution; metabolism; excretion (ADME)
  • Toxicology
  • Acute toxicity
  • See also
  • References

Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula and consists of four methyl groups (, denoted Me) attached to a central nitrogen atom. The cation is isoelectronic with neopentane (). 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.

==Common nomenclature== 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.

Excerpted from Wikipedia’s “tetramethylammonium” article, available under the CC BY-SA 4.0 licence.

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