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Details

Stereochemistry ACHIRAL
Molecular Formula C5H14NO.Cl
Molecular Weight 139.624
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHOLINE CHLORIDE

SMILES

[Cl-].C[N+](C)(C)CCO

InChI

InChIKey=SGMZJAMFUVOLNK-UHFFFAOYSA-M
InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C5H13NO
Molecular Weight 103.1628
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

CHOLINE is a basic constituent of lecithin that is found in many plants and animal organs. Choline was officially recognized as an essential nutrient by the Institute of Medicine in 1998.1 Its role in the body is complex. It is needed for neurotransmitter synthesis (acetylcholine), cell-membrane signaling (phospholipids), lipid transport (lipoproteins), and methyl-group metabolism (homocysteine reduction). It is the major dietary source of methyl groups via the synthesis of S-adenosylmethionine (AdoMet). At least 50 AdoMet-dependent reactions have been identified in mammals, and it is likely that the number is much higher. Choline is required to make the phospholipids phosphatidylcholine, lysophosphatidylcholine, choline plasmalogen, and sphingomyelin—essential components for all membranes. It plays important roles in brain and memory development in the fetus and appears to decrease the risk of the development of neural tube defects. The importance of choline in the diet extends into adulthood and old age. In a study of healthy adult subjects deprived of dietary choline, 77% of the men and 80% of the postmenopausal women developed signs of subclinical organ dysfunction (fatty liver or muscle damage). Less than half of premenopausal women developed such signs. Ten percent of the subjects studied developed fatty liver, muscle damage, or both when they consumed the Adequate Intake (AI) of choline. The damage was reversed when they consumed a high-choline diet. Plasma choline concentration has been found to vary in response to diet, decreasing approximately 30 percent in humans fed a choline-deficient diet for 3 weeks. Based on estimated dietary intakes and studies reporting liver damage with lower choline intakes, the Institute of Medicine, Food and Nutrition Board set the AI for choline at 425 milligrams/per day for women aged 19 and older, and 550 milligrams/per day for men aged 19 and older.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3013.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
GABAZOLAMINE
Primary
TRILIPIX
Primary
TRILIPIX
Primary
TRILIPIX

PubMed

Sample Use Guides

In Vivo Use Guide
Choline tablets will be taken at daily doses of 250 mg (in children with up to 40 kg body weight) and 500 mg (in children with more than 40 kg body weight).
Route of Administration: Oral
In Vitro Use Guide
Monolayer cultures of Primary bovine hepatocytes were maintained for 24 h and were approximately 80% confluent before exposure to treatment. Cells were randomly assigned to increasing concentrations (61, 128, 2028, and 4528 μmol/L) of choline chloride (CC), DL-methionine (DLM), and a fatty acid cocktail in a 4X4X2 factorial arrangement. All treatments were applied in triplicate in independent preparations of cells from 4 Holstein calves.
Substance Class Chemical
Record UNII
45I14D8O27
Record Status Validated (UNII)
Record Version