N,N-Dimethylethanolamine bitartrate

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N,N-Dimethylethanolamine (2R,3R)-bitartrate
N,N-Dimethylethanolamine (2R,3R)-bitartrate.png
Names
IUPAC name
N,N-Dimethylethanolamine (2R,3R)-bitartrate
Systematic IUPAC name
Dimethyl(2-hydroxyethyl)ammonium hydrogen 1,4-butanedioate
Other names
  • 2-(Dimethylamino)ethanol hydrogen L-(+)-Tartrate [1]
  • 2-(Dimethylamino)ethanol L-(+)-bitartrate [1]
  • 2-(Dimethylamino)ethanol (2R,3R)-2,3-dihydroxysuccinate [1]
  • Atrol [2]
  • Deanol bitartrate [1]
  • DMAE bitartrate [1]
  • Ethanol, 2-(dimethylamino)-, (2R,3R)-2,3-dihydroxybutanedioate (1:1) [3]
  • Liparon [4]
  • N,N-dimethylethanolamine L-(+)-bitartrate
  • N,N-Dimethylethanolamine (2R,3R)-bitartrate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.025.281 OOjs UI icon edit-ltr-progressive.svg
EC Number
PubChem CID
UNII
  • InChI=1S/C4H11NO.C4H6O6/c1-5(2)3-4-6;5-1(3(7)8)2(6)4(9)10/h6H,3-4H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
    Key: UIEGYKVRCKDVKQ-LREBCSMRSA-N
  • Isomeric:CN(C)CCO.C(C(C(=O)O)O)(C(=O)O)O
  • Non-isomeric:CN(C)CCO.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
Properties
C8H17NO7
Molar mass 239.224 g·mol−1
AppearanceWhite powder [4] [2] or white crystals [5]
Melting point 111–113 °C (232–235 °F; 384–386 K) [4]
Slightly [4]
Solubility Methanol (slightly, heated) [4]
Structure
Tetrahedral at the nitrogen atom
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Serious eye damage [1]
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P332, P337, P362+P364, P403+P233, P405, P501
Lethal dose or concentration (LD, LC):
  • 2600 mg/kg (rat, oral)
  • 3100 mg/kg (mouse, oral)
  • 3000 mg/kg (mouse, intraperitoneal)
[1] [2]
Related compounds
Other cations
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Contents

Chemistry

N,N-Dimethylethanolamine bitartrate is a N,N-dimethylethanolamine salt of tartaric acid. N,N-Dimethylethanolamine bitartrate contains tertiary ammonium cations (dimethyl(2-hydroxyethyl)ammonium [HN(CH3)2CH2CH2OH]+) and bitartrate anions (HOOC−CH(OH)−CH(OH)−COO). Tertiary ammonium cation is a cation in which three hydrogen atoms of ammonium are replaced with organyl groups. In this compound, the three substituents of ammonium are two 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).

Uses

N,N-Dimethylethanolamine bitartrate is used in biological studies to evaluate motor activity in response to the injection of N,N-dimethylethanolamine. [4]

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally 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.

In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions.

A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid gives a proton to a base—in other words, it is a base with a hydrogen ion added to it, as it loses a hydrogen ion in the reverse reaction. On the other hand, a conjugate base is what remains after an acid has donated a proton during a chemical reaction. Hence, a conjugate base is a substance formed by the removal of a proton from an acid, as it can gain a hydrogen ion in the reverse reaction. Because some acids can give multiple protons, the conjugate base of an acid may itself be acidic.

<span class="mw-page-title-main">Ammonium</span> Polyatomic ion (NH₄, charge +1)

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of 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.

<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 bananas, tamarinds, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. It 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.

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.

In organic chemistry, a carbanion is an anion in which carbon is negatively charged.

The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was first developed by Johannes Nicolaus Brønsted and Thomas Martin Lowry independently in 1923. The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory.

<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.

Acid salts are a class of salts that produce an acidic solution after being dissolved in a solvent. Its formation as a substance has a greater electrical conductivity than that of the pure solvent. An acidic solution formed by acid salt is made during partial neutralization of diprotic or polyprotic acids. A half-neutralization occurs due to the remaining of replaceable hydrogen atoms from the partial dissociation of weak acids that have not been reacted with hydroxide ions to create water molecules.

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

Dimethylethanolamine is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care products for improving skin tone and also taken orally as a nootropic. It is prepared by the ethoxylation of dimethylamine.

<span class="mw-page-title-main">Phosphoric acids and phosphates</span> Class of chemical species; phosphorus oxoacids and their deprotonated derivatives

In chemistry, a phosphoric acid, in the general sense, is a phosphorus oxoacid in which each phosphorus (P) atom is in the oxidation state +5, and is bonded to four oxygen (O) atoms, one of them through a double bond, arranged as the corners of a tetrahedron. Two or more of these PO4 tetrahedra may be connected by shared single-bonded oxygens, forming linear or branched chains, cycles, or more complex structures. The single-bonded oxygen atoms that are not shared are completed with acidic hydrogen atoms. The general formula of a phosphoric acid is Hn+2−2xPnO3n+1−x, where n is the number of phosphorus atoms and x is the number of fundamental cycles in the molecule's structure, between 0 and n + 2/2.

<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 bifunctional compound, meaning, it contains both quaternary ammonium functional group and a hydroxyl functional group. The cation 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">Eschenmoser's salt</span> Ionic compound with the formula [(H3C–)2N–CH2]I

In organic chemistry, Eschenmoser's salt is the ionic, organic compound [(CH3)2NCH2]I. It is the iodide salt of the dimethylaminomethylene cation [(CH3)2NCH2]+.

<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.

<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.

<span class="mw-page-title-main">Choline bitartrate</span> Choline bitartrate

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. It is hygroscopic when exposed to air. 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.

References