N,N-Dimethylethanolamine bitartrate

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N,N-Dimethylethanolamine (2R,3R)-bitartrate
N,N-Dimethylethanolamine (2R,3R)-bitartrate
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 Edit this at Wikidata
EC Number
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
Appearance White 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:
GHS07: Exclamation mark
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.

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]

References

  1. ^ a b c d e f g h i https://pubchem.ncbi.nlm.nih.gov/compound/Deanol-bitartrate
  2. ^ a b c https://www.sigmaaldrich.com/GB/en/sds/aldrich/39000
  3. ^ https://commonchemistry.cas.org/detail?cas_rn=5988-51-2
  4. ^ a b c d e f https://www.trc-canada.com/product-detail/?D471440
  5. ^ https://cymitquimica.com/cas/29870-28-8/
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