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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
    Choline
    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 Weight 104.17 g/mol
    Molecular Formula C5H14NO+
    XLogP3-0.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count2
    Exact Mass104.107539070 g/mol
    Monoisotopic Mass104.107539070 g/mol
    Topological Polar Surface Area20.2 Ų
    Heavy Atom Count7
    Formal Charge1
    Complexity46.5
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.

    API Reference Price

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    02-Jan-2021
    31-Aug-2024
    KGS
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    Quantity (KGS) & Unit rate (USD/KGS) over time

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