N,N-Dimethylethanolamine bitartrate

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.

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
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).
Infobox references

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]

Safety

N,N-Dimethylethanolamine bitartrate is flammable. Upon catching fire, it might release toxic gases, like carbon monoxide (CO), nitrogen monoxide (NO) and nitrogen dioxide (NO2). It may cause skin, eye and respiratory system irritation and a serious eye damage.[1]

References
  1. https://pubchem.ncbi.nlm.nih.gov/compound/Deanol-bitartrate
  2. https://www.sigmaaldrich.com/GB/en/sds/aldrich/39000
  3. https://commonchemistry.cas.org/detail?cas_rn=5988-51-2
  4. https://www.trc-canada.com/product-detail/?D471440
  5. https://cymitquimica.com/cas/29870-28-8/
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