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

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
CAS Number	5988-51-2 N
3D model (JSmol)	Isomeric: Interactive image Non-isomeric: Interactive image
ChemSpider	17340333
ECHA InfoCard	100.025.281
EC Number	227-809-3 [1]
PubChem CID	16212495
UNII	D240J05W14 [1]
CompTox Dashboard (EPA)	DTXSID40952332
InChI 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
SMILES 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
Chemical formula	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]
Solubility in water	Slightly[4]
Solubility	Methanol (slightly, heated)[4]
Structure
Coordination geometry	Tetrahedral at the nitrogen atom
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Serious eye damage[1]
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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):
LD50 (median dose)	2600 mg/kg (rat, oral) 3100 mg/kg (mouse, oral) 3000 mg/kg (mouse, intraperitoneal) [1][2]
Related compounds
Other cations	Choline bitartrate Sodium bitartrate Potassium bitartrate
Related compounds	Bitartrate Tartrate Tartaric acid
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]