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Chemistry

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Also known as: 87-67-2, 6k2w7t9v6y, Choline hydrogen l-(+)-tartrate, Choline tartrate, (2-hydroxyethyl)trimethylammonium-l-(+)-tartrate salt (1:1), Choline hydrogen tartrate
Molecular Formula
C9H19NO7
Molecular Weight
253.25  g/mol
InChI Key
QWJSAWXRUVVRLH-LREBCSMRSA-M
FDA UNII
6K2W7T9V6Y

Choline Tartrate
A basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism.
1 2D Structure

Choline Tartrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-hydroxyethyl(trimethyl)azanium;(2R,3R)-2,3,4-trihydroxy-4-oxobutanoate
2.1.2 InChI
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
2.1.3 InChI Key
QWJSAWXRUVVRLH-LREBCSMRSA-M
2.1.4 Canonical SMILES
C[N+](C)(C)CCO.C(C(C(=O)[O-])O)(C(=O)O)O
2.1.5 Isomeric SMILES
C[N+](C)(C)CCO.[C@@H]([C@H](C(=O)[O-])O)(C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
6K2W7T9V6Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-hydroxy-n,n,n-trimethylethanaminium

2. Bitartrate, Choline

3. Bursine

4. Chloride, Choline

5. Choline

6. Choline Chloride

7. Choline Citrate

8. Choline Hydroxide

9. Choline O Sulfate

10. Choline O-sulfate

11. Citrate, Choline

12. Fagine

13. Hydroxide, Choline

14. O-sulfate, Choline

15. Vidine

2.3.2 Depositor-Supplied Synonyms

1. 87-67-2

2. 6k2w7t9v6y

3. Choline Hydrogen L-(+)-tartrate

4. Choline Tartrate

5. (2-hydroxyethyl)trimethylammonium-l-(+)-tartrate Salt (1:1)

6. Choline Hydrogen Tartrate

7. 2-hydroxyethanaminium,-n,n,n-trimethyl-, (r-(r*,r*))-2,3-dihydroxybutanedioate (1:1)

8. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, (2r,3r)-2,3-dihydroxybutanedioate (1:1)

9. Choline, Tartrate (1:1)

10. Choline Bitartrate, Anhydrous

11. Hsdb 983

12. Choline, Tartrate (1:1) Salt

13. Tartaric Acid, Ion(1-), Choline

14. Einecs 201-763-4

15. Unii-6k2w7t9v6y

16. 2-hydroxy-n,n,n-trimethylethanaminium 2,3-dihydroxybutanedioate, (r-(r*,r*))-

17. 4-trihydroxy-4-oxobutanoate

18. Butanedioic Acid, 2,3-dihydroxy- (r-(r*,r*))-, Ion(1-), 2-hydroxy-n,n,n-trimethylethanaminium

19. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With (2r,3r)-2,3-dihydroxybutanedioic Acid (1:1)

20. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With (r-(r*,r*))-2,3-dihydroxybutanedioic Acid (1:1)

21. Schembl225594

22. Choline (as Bitartrate)

23. Choline Bitartrate [mi]

24. 2-hydroxyethyl(trimethyl)azanium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate

25. Choline Bitartrate [fcc]

26. Choline Bitartrate [hsdb]

27. Dtxsid00889332

28. Choline Bitartrate [vandf]

29. 2-hydroxyethyl(trimethyl)azanium;2

30. Choline Bitartrate [mart.]

31. Choline Bitartrate [usp-rs]

32. Choline Bitartrate [who-dd]

33. S4703

34. Ccg-266986

35. Choline (as Bitartrate) [vandf]

36. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With (theta-(theta,theta))-2,3-dihydroxybutanedioic Acid (1:1)

37. Hy-101036

38. Cs-0020747

39. F71308

40. Q18324709

41. Choline Bitartrate, United States Pharmacopeia (usp) Reference Standard

42. 2-hydroxy-n,n,n-trimethylethan-1-aminium (2r,3r)-3-carboxy-2,3-dihydroxypropanoate

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 253.25 g/mol
Molecular Formula C9H19NO7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass253.11615195 g/mol
Monoisotopic Mass253.11615195 g/mol
Topological Polar Surface Area138 Ų
Heavy Atom Count17
Formal Charge0
Complexity193
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Some clinical improvement with choline treatment has also been reported in huntington's chorea...in gilles de la tourette's disease, in friedreich's ataxia, & in presenile dementia ... /Choline/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1575


A nutrient and/or dietary supplement food additive

Sax, N.I. Dangerous Properties of Industrial Materials. 5th ed. New York: Van Nostrand Rheinhold, 1979., p. 503


/EXPL THER/ Eight lithium-treated patients with DSM-IV bipolar disorder, rapid cycling type were randomly assigned to 50 mg/kg/day of choline bitartrate or placebo for 12 weeks. Brain purine, choline and lithium levels were assessed using 1H- and 7Li-MRS. Patients received four to six MRS scans, at baseline and weeks 2, 3, 5, 8, 10 and 12 of treatment (n = 40 scans). Patients were assessed using the Clinical Global Impression Scale (CGIS), the Young Mania Rating Scale (YRMS) and the Hamilton Depression Rating Scale (HDRS) at each MRS scan. ... There were no significant differences in change-from-baseline measures of CGIS, YMRS, and HDRS, brain choline/creatine ratios, and brain lithium levels over a 12-week assessment period between the choline and placebo groups or within each group. However, the choline treatment group showed a significant decrease in purine metabolite ratios from baseline (purine/n-acetyl aspartate: coef = -0.08, z = -2.17, df = 22, p = 0.030; purine/choline: coef = -0.12, z = -1.97, df = 22, p = 0.049) compared to the placebo group, controlling for brain lithium level changes. Brain lithium level change was not a significant predictor of purine ratios. ... The current study reports that oral choline supplementation resulted in a significant decrease in brain purine levels over a 12-week treatment period in lithium-treated patients with DSM-IV bipolar disorder, rapid-cycling type, which may be related to the anti-manic effects of adjuvant choline. This result is consistent with mitochondrial dysfunction in bipolar disorder inadequately meeting the demand for increased ATP production as exogenous oral choline administration increases membrane phospholipid synthesis.

PMID:12895208 Lyoo IK et al; Bipolar Disord 5 (4): 300-6 (2003)


/EXPL THER/ ... Choline bitartrate was given openly to 6 consecutive lithium-treated outpatients with rapid-cycling bipolar disorder. Five patients also underwent brain proton magnetic resonance spectroscopy. Five of 6 rapid-cycling patients had a substantial reduction in manic symptoms, and 4 patients had a marked reduction in all mood symptoms during choline therapy. The patients who responded to choline all exhibited a substantial rise in the basal ganglia concentration of choline-containing compounds. Choline was well tolerated in all cases. Choline, in the presence of lithium, was a safe and effective treatment for 4 of 6 rapid-cycling patients in our series. A hypothesis is suggested to explain both lithium refractoriness in patients with bipolar disorder and the action of choline in mania, which involves the interaction between phosphatidylinositol and phosphatidylcholine second-messenger systems.

PMID:8874839 Stoll AL et al; Biol Psychiatry 40 (5): 382-8 (1996)


For more Therapeutic Uses (Complete) data for CHOLINE BITARTRATE (6 total), please visit the HSDB record page.


4.2 Minimum/Potential Fatal Human Dose

Oral LD50 for man is estimated to be of the order of 200-400 g. /CHOLINE/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1575


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Nootropic Agents

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)


Lipotropic Agents

Endogenous factors or drugs that increase the transport and metabolism of LIPIDS including the synthesis of LIPOPROTEINS by the LIVER and their uptake by extrahepatic tissues. (See all compounds classified as Lipotropic Agents.)


5.2 Absorption, Distribution and Excretion

Choline is absorbed from diet as such or as lecithin. Latter is hydrolyzed by intestinal mucosa to glycerophosphoryl choline, which either passes to liver to liberate choline or to peripheral tissues via intestinal lymphatics. /Choline/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1575


Choline are absorbed via the portal circulation ... The liver takes up the majority of choline and stores it in the form of phosphatidylcholine and sphingomyelin. Kidney and brain also accumulate choline ... Some free choline is excreted with urine ... A specific carrier is needed for the transport of free choline across the blood-brain barrier, and the capacity is especially high in neonates. /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 106 (2005)


Free choline is transported across the blood-brain barrier at a rate that is proportional to serum choline level ... In advanced age ... brain choline uptake /is decr/ ... /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 107 (2005)


During pregnancy, large amt of choline are delivered to the fetus across the placenta and this depletes maternal stores. Choline concn in amniotic fluid is 10-fold greater than that in maternal blood. At birth, humans and other mammals have plasma choline concn that are much higher than those in adults ... In rats, the liver choline concn in late pregnancy decr to less than one-third that of nonpregnant females ... /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 108 (2005)


For more Absorption, Distribution and Excretion (Complete) data for CHOLINE BITARTRATE (8 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Free choline is not fully absorbed, especially after large doses, and intestinal bacteria metabolize choline to trimethylamine. /Choline/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1575


/The/ ability to form choline /de novo via the methylation of phosphatidylethanolamine using S-adenosylmethionine as the methyl donor, mostly in the liver,/ means that some of the demand for choline can ... be met using methyl groups derived from 1-carbon metabolism (via methyl-folate and methionine). Several vitamins (folate, vitamin B12, vitamin B6, and riboflavin) and the amino acid methionine interact with choline in 1-carbon metabolism ... Methionine, methyl-tetrahydrofolate (THF), and choline can be fungible sources of methyl groups. /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 105 (2005)


Before choline can be absorbed in the gut, some is metabolized by bacteria to form betaine and methylamines (which are not methyl donors) ... Although some free choline is excreted with urine, most is oxidized in the kidney to form betaine ... /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 106 (2005)


Acetylcholine is one of the most important neurotransmitters used by neurons in the memory centers of the brain (hippocampus and septum). Choline accelerates the synth and release of acetylcholine in nerve cells. Choline used by brain neurons is largely derived from membrane lecithin /(phosphatidylcholine)/, or from dietary intake of choline and lecithin ... Choline derived from lecithin may be especially important when extracellular choline is in short supply, as might be expected to occur in advanced age because of decr brain choline uptake ... /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 107 (2005)


For more Metabolism/Metabolites (Complete) data for CHOLINE BITARTRATE (6 total), please visit the HSDB record page.


5.4 Mechanism of Action

Several mechanisms are suggested for the cancer-promoting effect of a choline-devoid diet. These incl incr cell proliferation related to regeneration after parenchymal cell death occurs in the choline deficient liver, hypomethylation of DNA (alters expression of genes), reactive oxygen species leakage from mitochondria with incr lipid peroxidation in liver, activation of protein kinase C signaling due to accumulation of diacylglycerol in liver, mutation of the fragile histidine triad (FHIT) gene, which is a tumor suppressor gene, and defective cell-suicide (apoptosis) mechanisms. Loss of phposphatidylethanolamine N-methyl-transferase (PEMT) function may also contribute to malignant transformation of hepatocytes. /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 107 (2005)


Acetylcholine is one of the most important neurotransmitters used by neurons in the memory centers of the brain (hippocampus and septum). Choline accelerates the synth and release of acetylcholine in nerve cells. /Choline/

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 107 (2005)


... Choline deficiency in cell culture causes apoptosis or programmed cell death. This appears to be due to abnormalities in cell membrane phosphatidylcholine content and an incr in ceramide, a precursor, as well as a metabolite of sphingomyelin. Ceramide accumulation, which is caused by choline deficiency, appears to activate a caspase, a type of enzyme that mediates apoptosis. /Choline/

Thomson Healthcare. PDR for Nutritional Supplements. Thomson Health Care Inc. Montvale, NJ. p.90 (2001)


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