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Choline (ˈkoʊliːn ) is a cation with the chemical formula . Choline forms various salts, for example choline chloride and choline bitartrate. Choline is a quaternary ammonium cation. The cholines are a family of water-soluble quaternary ammonium compounds. Choline is the parent compound of the cholines class, consisting of ethanolamine residue having three methyl groups attached to the same nitrogen atom. Choline hydroxide is known as choline base. It is hygroscopic and thus often encountered as a colorless viscous hydrated syrup that smells of trimethylamine (TMA). Aqueous solutions of choline are stable, but the compound slowly breaks down to ethylene glycol, polyethylene glycols, and TMA. Choline chloride can be made by treating TMA with 2-chloroethanol: The 2-chloroethanol can be generated from ethylene oxide. Choline has historically been produced from natural sources, such as via hydrolysis of lecithin. Choline is widespread in nature in living beings. In most animals, choline phospholipids are necessary components in cell membranes, in the membranes of cell organelles, and in very low-density lipoproteins. Choline is an essential nutrient for humans and many other animals. Humans are capable of some de novo synthesis of choline but require additional choline in the diet to maintain health. Dietary requirements can be met by choline by itself or in the form of choline phospholipids, such as phosphatidylcholine. Choline is not formally classified as a vitamin despite being an essential nutrient with an amino acid–like structure and metabolism. Choline is required to produce acetylcholine – a neurotransmitter – and S-adenosylmethionine (SAM), a universal methyl donor. Upon methylation SAM is transformed into S-adenosyl homocysteine. Symptomatic choline deficiency causes non-alcoholic fatty liver disease and muscle damage. Excessive consumption of choline (greater than 7.5 grams per day) can cause low blood pressure, sweating, diarrhea and fish-like body smell due to trimethylamine, which forms in the metabolism of choline.

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