Structure via PubChem · Public domain (PubChem)
tetramethylammonium
Sign in to saveTetramethylammonium (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
Research
2,083 papers- Sleep drives metabolite clearance from the adult brain.Science (New York, N.Y.) · 2013
- Tetramethylammonium Fluoride Alcohol Adducts for S(N)Ar Fluorination.Organic letters · 2021
- Syntheses of pure tetramethylammonium peroxynitrite.Methods in enzymology · 1996
- Tetramethylammonium hydroxide poisoning.Clinical toxicology (Philadelphia, Pa.) · 2010
- Anaerobic hydrolysis of recalcitrant tetramethylammonium from semiconductor wastewater: Performance and mechanisms.Journal of hazardous materials · 2023
via PubMed
Wikidata facts
- Subclass of
- quaternary ammonium cation
- 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⁺
via Wikidata · CC0
~7 min read
Encyclopedic overview
9 sectionsContents
- 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.