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Choline C-11

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Chemistry

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Also known as: Choline ion, Bilineurine, 62-49-7, Choline cation, 2-hydroxy-n,n,n-trimethylethanaminium, Cholinum

Molecular Formula

C₅H₁₄NO+

Molecular Weight

104.17 g/mol

InChI Key

OEYIOHPDSNJKLS-UHFFFAOYSA-N

FDA UNII

N91BDP6H0X

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

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxyethyl(trimethyl)azanium

2.1.2 InChI

InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1

2.1.3 InChI Key

OEYIOHPDSNJKLS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C[N+](C)(C)CCO

2.2 Other Identifiers

2.2.1 UNII

N91BDP6H0X

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 Bitartrate

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. Choline Ion

2. Bilineurine

3. 62-49-7

4. Choline Cation

5. 2-hydroxy-n,n,n-trimethylethanaminium

6. Cholinum

7. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-

8. (2-hydroxyethyl)trimethylammonium

9. Trimethylethanolamine

10. N-trimethylethanolamine

11. Vitamin J

12. 2-hydroxyethyl(trimethyl)azanium

13. Ccris 5847

14. Ai3-24208

15. Brn 1736748

16. N,n,n-trimethylethanol-ammonium

17. Chebi:15354

18. (beta-hydroxyethyl)trimethylammonium

19. Chembl920

20. N91bdp6h0x

21. (2-hydroxyethyl)trimethylazanium

22. 2-hydroxy-n,n,n-trimethyl-ethanaminium

23. Bilineurine; Choline Cation; Choline Ion; Nanoveson C; Vitamin J

24. Cht

25. Nsc402838

26. Ncgc00015219-03

27. Einecs 200-535-1

28. Unii-n91bdp6h0x

29. 2-hydroxyethyl(trimethyl)ammonium

30. 1oba

31. 2reg

32. 3ppq

33. Choline (dcf)

34. Choline (8ci)

35. Nanoveson C

36. Spectrum_000258

37. 2ha3

38. 3r6u

39. Choline [vandf]

40. Choline [mi]

41. Spectrum2_001938

42. Spectrum4_000867

43. Spectrum5_001579

44. Lopac-c-1754

45. Choline [who-dd]

46. Bmse000285

47. Bmse000953

48. Bmse001003

49. Epitope Id:116046

50. Schembl3142

51. Lopac0_000180

52. Kbiogr_001533

53. Kbioss_000738

54. 3-04-00-00651 (beilstein Handbook Reference)

55. Divk1c_000107

56. N,n,n-trimethylethanolammonium

57. Spbio_001975

58. Gtpl4551

59. Dtxsid8043789

60. Kbio1_000107

61. Kbio2_000738

62. Kbio2_003306

63. Kbio2_005874

64. Nsc6393

65. Ninds_000107

66. (2-hydroxyethyl)trimethyl Ammonium

67. Mono-2-hydroxyethyltrimethylammonium

68. Nsc-6393

69. Zinc3079337

70. Bbl005532

71. Bdbm50026220

72. Stl137772

73. Akos005721137

74. 2-hydroxyethyl)trimethylammonium

75. Ccg-204275

76. Db00122

77. Idi1_000107

78. Ncgc00015219-01

79. Ncgc00015219-02

80. Ncgc00015219-04

81. Ncgc00015219-07

82. Ncgc00015219-10

83. Ncgc00162082-01

84. Carbachol Impurity A [ep Impurity]

85. Sbi-0050168.p003

86. 2-hydroxy-n,n,n-trimethylammonium Chloride

87. (.beta.-hydroxyethyl)trimethylammonium

88. C00114

89. D07690

90. Ab00053822_02

91. Ethanaminium, 2-hydroxy-n,n,n-trimethyl- (9ci)

92. Q193166

93. Acetylcholine Chloride Impurity A [ep Impurity]

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₅H₁₄NO+
Molecular Weight	104.17 g/mol
XLogP3	-0.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	104.107539070 g/mol
Monoisotopic Mass	104.107539070 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	7
Formal Charge	1
Complexity	46.5
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

5 Pharmacology and Biochemistry

5.1 Pharmacology

This compound is needed for good nerve conduction throughout the CNS (central nervous system) as it is a precursor to acetylcholine (ACh). Choline is also needed for gallbladder regulation, liver function and lecithin (a key lipid) formation. Choline also aids in fat and cholesterol metabolism and prevents excessive fat build up in the liver. Choline has been used to mitigate the effects of Parkinsonism and tardive dyskinesia. Choline deficiencies may result in excessive build-up of fat in the liver, high blood pressure, gastric ulcers, kidney and liver dysfunction and stunted growth.

5.2 MeSH Pharmacological Classification

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.)

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.)

5.3 Metabolism/Metabolites

Choline has known human metabolites that include Trimethylazanium and acetaldehyde.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.4 Mechanism of Action

Choline is a major part of the polar head group of phosphatidylcholine. Phosphatidylcholine's role in the maintenance of cell membrane integrity is vital to all of the basic biological processes: information flow, intracellular communication and bioenergetics. Inadequate choline intake would negatively affect all these processes. Choline is also a major part of another membrane phospholipid, sphingomyelin, also important for the maintenance of cell structure and function. It is noteworthy and not surprising that 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 increase in ceramide, a precursor, as well as a metabolite, of sphingomyelin. Ceramide accumulation, which is caused by choline deficiency, appears to activate Caspase, a type of enzyme that mediates apoptosis. Betaine or trimethylglycine is derived from choline via an oxidation reaction. Betaine is one of the factors that maintains low levels of homocysteine by resynthesizing L-methionine from homocysteine. Elevated homocysteine levels are a significant risk factor for atherosclerosis, as well as other cardiovascular and neurological disorders. Acetylcholine is one of the major neurotransmitters and requires choline for its synthesis. Adequate acetylcholine levels in the brain are believed to be protective against certain types of dementia, including Alzheimer's disease.

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