Английская Википедия:Choline bitartrate

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Choline bitartrate is an organic compound with the chemical formula Шаблон:Chem2. It is a white crystalline powder with an acid taste. It is hygroscopic when exposed to air. Modern texts refer to the choline salt of the natural form of tartaric acid, that is, the salt called choline dextrobitartrate, choline (2R,3R)-bitartrate or choline L-(+)-bitartrate.

Chemistry

Choline bitartrate is a choline salt of tartaric acid. Choline bitartrate contains quaternary ammonium cations ((2-hydroxyethyl)trimethylammonium Шаблон:Chem2) and bitartrate anions (Шаблон:Chem2). Quaternary ammonium cation is a cation in which all four hydrogen atoms of ammonium are replaced with organyl groups. In the choline cation, the four substituents of ammonium are three methyl groups (Шаблон:Chem2) and one 2-hydroxyethyl group (Шаблон:Chem2). The bitartrate anion is chiral (there are left, right and meso forms of bitartrate, see tartaric acid).

Production

Choline bitartrate can be produced by the chemical reaction of trimethylamine with ethylene oxide and water, followed by reaction with tartaric acid.

Uses

Choline bitartrate is used as a dietary supplement, a food additive, a nutrient and as a lipotropic compound. It is also used as a medication against bipolar disorder and mania (see: choline). Certain conducted double-blind, placebo-controlled studies of the effects of choline bitartrate treatment against Alzheimer-type dementias suggest improvement in some areas of patients' cognitive performance.

Safety

Choline bitartrate is flammable. Upon catching a fire, choline bitartrate may release toxic gases, like carbon monoxide (CO), carbon dioxide (Шаблон:Chem2) and nitrogen oxides (NO, Шаблон:Chem2). May react violently with strong oxidizing agents.

The toxicity of this compound is similar to toxicity of choline itself, which is fairly low, and it is used as a dietary supplement. Oral LD₅₀ value for a human is estimated to be 200 to 400 grams (as choline). Nevertheless, choline bitartrate can be harmful, if absorbed through skin. It may cause skin, eye and respiratory system irritation. May cause gastrointestinal system irritation as well. If swallowed in high doses, may cause dizziness, nausea, vomiting and diarrhea, and a rotten fish-like body smell resulting from the excretion of trimethylamine from the body (trimethylamine is a choline metabolite). There are reports of depression or increased symptoms of it in patients using high doses of choline bitartrate. When choline bitartrate is used appropriately, hazardous effects are unlikely to occur.

References

Шаблон:Organic-compound-stub