Choline bitartrate

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Choline (2R,3R)-bitartrate
Choline (2R,3R)-bitartrate.png
Names
IUPAC name
Choline (2R,3R)-bitartrate
Systematic IUPAC name
(2-Hydroxyethyl)trimethylaminium hydrogen (2R,3R)-tartrate [1]
Other names
  • Choline hydrogen L-(+)-tartrate [2]
  • Choline (2R,3R)-tartrate (1:1) [2]
  • (2-Hydroxyethyl)trimethylammonium hydrogen (2R,3R)-tartrate [2]
  • (2-Hydroxyethyl)trimethylammonium L-(+)-bitartrate
  • (2-Hydroxyethyl)trimethylammonium (2R,3R)-bitartrate
  • (2-Hydroxyethyl)trimethylammonium L-(+)-tartrate salt (1:1) [2]
Identifiers
3D model (JSmol)
ECHA InfoCard 100.001.604 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • [2] :InChI=1S/C5H14NO.C4H6O6/c1-6(2,3)4-5-7;5-1(3(7)8)2(6)4(9)10/h7H,4-5H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/q+1;/p-1/t;1-,2-/m.1/s1
    Key: QWJSAWXRUVVRLH-LREBCSMRSA-M
  • Non-isomeric:C[N+](C)(C)CCO.C(C(C(=O)[O-])O)(C(=O)O)O
  • Isomeric:C[N+](C)(C)CCO.[C@@H]([C@H](C(=O)[O-])O)(C(=O)O)O
Properties
C9H19NO7
Molar mass 253.251 g·mol−1
AppearanceWhite crystalline powder [2] [1]
Odor Odorless or faint trimethylamine-like odor [2]
Melting point 147–153 °C (297–307 °F; 420–426 K) [2] [1]
Solubility Water (slightly), ethanol (slightly), DMSO (slightly), methanol (slightly, when heated); insoluble in diethyl ether, chloroform and benzene [2] [1]
Structure
Tetrahedral molecular geometry at the nitrogen atom
Hazards
Lethal dose or concentration (LD, LC):
200 to 400 grams (as choline, human, estimated) [2]
Related compounds
Other anions
Other cations
N,N-Dimethylethanolamine bitartrate
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Choline bitartrate is an organic compound with the chemical formula [(CH3)3NCH2CH2OH]+HOOC−CH(OH)−CH(OH)−COO. It is a white crystalline powder with an acid taste. [2] It is hygroscopic when exposed to air. [2] Modern texts refer to the choline salt of the natural form of tartaric acid, that is, the salt called choline dextrobitartrate, choline (2R,3R)-bitartrate or choline L-(+)-bitartrate.

Contents

Chemistry

Choline bitartrate is a choline salt of tartaric acid. Choline bitartrate contains quaternary ammonium cations ((2-hydroxyethyl)trimethylammonium [(CH3)3NCH2CH2OH]+) and bitartrate anions (HOOC−CH(OH)−CH(OH)−COO). Quaternary ammonium cation is a cation in which all four hydrogen atoms of ammonium are replaced with organyl groups. [3] In the choline cation, the four substituents of ammonium are three methyl groups (−CH3) and one 2-hydroxyethyl group (−CH2CH2OH). The bitartrate anion is chiral (there are left, right and meso forms of bitartrate, see tartaric acid).

Production

Choline bitartrate can be produced by the chemical reaction of trimethylamine with ethylene oxide and water, followed by reaction with tartaric acid. [2]

N(CH3)3 + CH2CH2O + H2O → [(CH3)3NCH2CH2OH]+OH [(CH3)3NCH2CH2OH]+OH + C4H6O6[(CH3)3NCH2CH2OH]+C4H5O6 + H2O

Uses

Choline bitartrate is used as a dietary supplement, a food additive, a nutrient and as a lipotropic compound. [2] [4] It is also used as a medication against bipolar disorder and mania (see: choline). [2] Certain conducted double-blind, placebo-controlled studies of the effects of choline bitartrate treatment against Alzheimer-type dementias suggest improvement in some areas of patients' cognitive performance. [5]

Safety

Choline bitartrate is flammable. When burned, choline bitartrate may release toxic gases, like carbon monoxide (CO), carbon dioxide (CO2) and nitrogen oxides (NO, NO2). May react violently with strong oxidizing agents. [1] [6] [7]

The toxicity of this compound is similar to toxicity of choline itself, which is fairly low, and it is used as a dietary supplement. Oral LD50 value for a human is estimated to be 200 to 400 grams (as choline). Nevertheless, choline bitartrate can be harmful, if absorbed through skin. It may cause skin, eye and respiratory system irritation. May cause gastrointestinal system irritation as well. If swallowed in high doses, may cause dizziness, nausea, vomiting and diarrhea, and a rotten fish-like body smell resulting from the excretion of trimethylamine from the body (trimethylamine is a choline metabolite). There are reports of depression or increased symptoms of it in patients using high doses of choline bitartrate. When choline bitartrate is used appropriately, hazardous effects are unlikely to occur. [2] [1] [6] [7]

Related Research Articles

<span class="mw-page-title-main">Amine</span> Chemical compounds and groups containing nitrogen with a lone pair (:N)

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Formally, amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Ammonium</span> Chemical compound

Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) molecular ion with the chemical formula NH+4 or [NH4]+. It is formed by the addition of a proton to ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups. Not only is ammonium a source of nitrogen and a key metabolite for many living organisms, but it is an integral part of the global nitrogen cycle. As such, human impact in recent years could have an effect on the biological communities that depend on it.

<span class="mw-page-title-main">Tartaric acid</span> Organic acid found in many fruits

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. Potassium bitartrate is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic chemical synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.

<span class="mw-page-title-main">Choline</span> Chemical compound and essential nutrient

Choline ( KOH-leen) is an essential nutrient for humans and many other animals, which was formerly classified as a B vitamin (vitamin B4). It is a structural part of phospholipids and a methyl donor in metabolic one-carbon chemistry. The compound is related to trimethylglycine in the latter respect. It is a cation with the chemical formula [(CH3)3NCH2CH2OH]+. Choline forms various salts, for example choline chloride and choline bitartrate.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

<span class="mw-page-title-main">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

<span class="mw-page-title-main">Trimethylamine</span> Chemical compound responsible for rotten fish odor

Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry. At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact. At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.

<span class="mw-page-title-main">Ammonium chlorate</span> Chemical compound

Ammonium chlorate is an inorganic compound with the formula NH4ClO3.

<span class="mw-page-title-main">Choline chloride</span> Chemical compound

Choline chloride is an organic compound with the formula [(CH3)3NCH2CH2OH]+Cl. It is a quaternary ammonium salt, consisting of choline cations and chloride anions. It is a bifunctional compound, meaning, it contains both a quaternary ammonium functional group and a hydroxyl functional group. The anion of this salt, choline, occurs in nature in living beings. Choline chloride is a white, water-soluble salt used mainly in animal feed.

<span class="mw-page-title-main">Tartrate</span> Chemical compound

A tartrate is a salt or ester of the organic compound tartaric acid, a dicarboxylic acid. The formula of the tartrate dianion is OOC-CH(OH)-CH(OH)-COO or C4H4O62−.

<span class="mw-page-title-main">Tetramethylammonium hydroxide</span> Chemical compound

Tetramethylammonium hydroxide (TMAH or TMAOH) is a quaternary ammonium salt with molecular formula N(CH3)4+ OH. It is commonly encountered in form of concentrated solutions in water or methanol. TMAH in solid state and its aqueous solutions are all colorless, but may be yellowish if impure. Although TMAH has virtually no odor when pure, samples often have a strong fishy smell due to presence of trimethylamine which is a common impurity. TMAH has several diverse industrial and research applications.

In chemistry, an onium ion is a cation formally obtained by the protonation of mononuclear parent hydride of a pnictogen, chalcogen, or halogen. The oldest-known onium ion, and the namesake for the class, is ammonium, NH+4, the protonated derivative of ammonia, NH3.

Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic mixture into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term with the same meaning is optical resolution.

An organic base is an organic compound which acts as a base. Organic bases are usually, but not always, proton acceptors. They usually contain nitrogen atoms, which can easily be protonated. For example, amines or nitrogen-containing heterocyclic compounds have a lone pair of electrons on the nitrogen atom and can thus act as proton acceptors. Examples include:

<span class="mw-page-title-main">Monosodium tartrate</span> Chemical compound

Monosodium tartrate or sodium bitartrate is a sodium acid salt of tartaric acid. As a food additive it is used as an acidity regulator and is known by the E number E335. As an analytical reagent, it can be used in a test for ammonium cation which gives a white precipitate.

<span class="mw-page-title-main">Tetraethylammonium chloride</span> Chemical compound

Tetraethylammonium chloride (TEAC) is a quaternary ammonium compound with the chemical formula [N(CH2CH3)4]+Cl, sometimes written as [NEt4]Cl. In appearance, it is a hygroscopic, colorless, crystalline solid. It has been used as the source of tetraethylammonium ions in pharmacological and physiological studies, but is also used in organic chemical synthesis.

<span class="mw-page-title-main">Tetramethylammonium</span> Polyatomic ion (N(CH₃)₄, charge +1)

Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula [Me4N]+ and consists of four methyl groups 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.

<span class="mw-page-title-main">Bitartrate</span> Chemical compound

Bitartrate is an anion which is the conjugate base of tartaric acid. It may also refer to any salt or monoester of tartaric acid.

<span class="mw-page-title-main">Choline hydroxide</span> Organic chemical compound

Choline hydroxide is an organic compound with the chemical formula [(CH3)3NCH2CH2OH]+OH. It is also known as choline base. It is used as solutions in water or alcohols, which are colorless and very alkaline.

<i>N</i>,<i>N</i>-Dimethylethanolamine bitartrate Chemical compound

N,N-Dimethylethanolamine bitartrate or deanol bitartrate is an organic compound with the chemical formula [HN(CH3)2CH2CH2OH]+HOOC−CH(OH)−CH(OH)−COO. It is a white powder. Modern texts refer to the N,N-dimethylethanolamine salt of the natural form of tartaric acid, that is, the salt called N,N-dimethylethanolamine dextrobitartrate, N,N-dimethylethanolamine (2R,3R)-bitartrate or N,N-dimethylethanolamine L-(+)-bitartrate.

References

  1. 1 2 3 4 5 6 https://www.trc-canada.com/prod-img/MSDS/C432640MSDS.pdf
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 "Choline bitartrate". pubchem.ncbi.nlm.nih.gov.
  3. IUPAC , Compendium of Chemical Terminology , 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006) " quaternary ammonium compounds ". doi : 10.1351/goldbook.Q05003
  4. "87-67-2 | Choline Bitartrate | Choline Tartrate; Choline Hydrogen Tartrate; Choline Tartrate (1:1); 2-Hydroxy-N,N,N-trimethyl-Ethanaminium Salt with (2R,3R)-2,3-dihydroxybutanedioic acid (1:1); , 2-Hydroxy-N,N,N-trimethylethanaminium Salt with [R-(R*,R*)]-2,3-dihydroxybutanedioic Acid (1:1); (2R,3R)-2,3-Dihydroxybutanedioic Acid Ion(1-) 2-Hydroxy-N,N,N-trimethylethanaminium; [R-(R*,R*)]-2,3-Dihydroxybutanedioic Acid Ion(1-), 2-Hydroxy-N,N,N-trimethylethanaminium; Tartaric acid Ion(1-) Choline; (2-Hydroxyethyl)trimethylammonium Bitartrate; | C₉H₁₉NO₇ | TRC".
  5. "APA PsycNet". psycnet.apa.org.
  6. 1 2 https://www.sigmaaldrich.com/GB/en/sds/usp/1133536
  7. 1 2 https://www.oxfordlabchem.com/msds/(C-02684)%20CHOLINE%20BITARTRATE.pdf