Choline bitartrate

Choline (2R,3R)-bitartrate

Names
IUPAC name Choline (2R,3R)-bitartrate
Systematic IUPAC name (2-Hydroxyethyl)trimethylaminium hydrogen (2R,3R)-tartrate[2]
Other names Choline hydrogen L-(+)-tartrate[1] Choline (2R,3R)-tartrate (1:1)[1] (2-Hydroxyethyl)trimethylammonium hydrogen (2R,3R)-tartrate[1] (2-Hydroxyethyl)trimethylammonium L-(+)-bitartrate (2-Hydroxyethyl)trimethylammonium (2R,3R)-bitartrate (2-Hydroxyethyl)trimethylammonium L-(+)-tartrate salt (1:1)[1]
Identifiers
CAS Number	87-67-2
3D model (JSmol)	Non-isomeric: Interactive image Isomeric: Interactive image
ECHA InfoCard	100.001.604
PubChem CID	6900
UNII	6K2W7T9V6Y [1]
CompTox Dashboard (EPA)	DTXSID00889332
InChI [1]: 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
SMILES 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
Chemical formula	C9H19NO7
Molar mass	253.251 g·mol−1
Appearance	White crystalline powder[1][2]
Odor	Odorless or faint trimethylamine-like odor[1]
Melting point	147–153 °C (297–307 °F; 420–426 K)[1][2]
Solubility	Water (slightly), ethanol (slightly), DMSO (slightly), methanol (slightly, when heated); insoluble in diethyl ether, chloroform and benzene[1][2]
Structure
Coordination geometry	Tetrahedral molecular geometry at the nitrogen atom
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	200 to 400 grams (as choline, human, estimated)[1]
Related compounds
Other anions	Choline chloride Choline hydroxide
Other cations	N,N-Dimethylethanolamine bitartrate
Related compounds	Choline Ethanolamine Tartaric acid Trimethylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1] It is hygroscopic when exposed to air.^[1] 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.