Editing Choline (section)

{{short description|Chemical compound and essential nutrient}}
{{Distinguish|chlorine}}
{{Use American English|date=November 2024}}
{{cs1 config|name-list-style=vanc|display-authors=3}}
{{Use dmy dates|date=September 2020}}
{{chembox
|Watchedfields = changed
|verifiedrevid = 477165756
|ImageFile = Choline cation.png
|ImageAlt = Choline cation skeletal formula
|ImageName = Choline cation skeletal formula
|ImageClass = skin-invert-image
|ImageFile1 = Choline-cation-3D-balls.png
|ImageSize1 = 180
|ImageAlt1 = Ball-and-stick model
|IUPACName = 2-Hydroxyethyl(trimethyl)azanium<ref name="pubchem">{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Choline|publisher=PubChem, National Library of Medicine, US National Institutes of Health|date=26 October 2024|accessdate=31 October 2024 | title=Choline }}</ref>
|PIN = 2-Hydroxy-''N'',''N'',''N''-trimethylethan-1-aminium
|OtherNames = {{ubl|Bilineurine|(2-Hydroxyethyl)trimethylammonium|2-Hydroxy-''N'',''N'',''N''-trimethylethanaminium}}
|Section1={{Chembox Identifiers
|IUPHAR_ligand = 4551
|Beilstein = 1736748
|CASNo = 62-49-7
|CASNo_Ref = {{cascite|correct|??}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 15354
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 299
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank = DB00122
|EC_number = 200-535-1
|Gmelin = 324597
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C00114
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = N91BDP6H0X
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 920
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = OEYIOHPDSNJKLS-UHFFFAOYSA-N
|PubChem = 305
|SMILES = C[N+](C)(C)CCO
}}
|Section2={{Chembox Properties
|Appearance = 
|Formula = {{chem2|[(CH3)3NCH2CH2OH]+}}
|C=5|H=14|N=1|O=1
|Solubility = 
|SolubleOther = 
}}
|Section3={{Chembox Structure
|Coordination = [[Tetrahedral molecular geometry|Tetrahedral]] at the [[nitrogen]] atom
}}
|Section4={{Chembox Hazards
|ExternalSDS = 4
|LD50 = 3–6 g/kg (rat, oral)<ref name="lpi"/>
|MainHazards = [[Corrosive]]
|NFPA-S = COR
|NFPA-F = 1
|NFPA-R = 0
|NFPA-H = 3
|GHSPictograms = {{GHS05}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|314}}
|PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}}
}}
}}

'''Choline''' is a [[cation]] with the [[chemical formula]] {{chem2|[(CH3)3NCH2CH2OH]+}}.<ref name=pubchem/><ref name="lpi">{{cite book |doi=10.1002/0471238961.0308151207090404.a01 |chapter=Choline |title=Kirk-Othmer Encyclopedia of Chemical Technology |date=2000 |last1=Gidding |first1=Curtis E. |isbn=978-0-471-48494-3 }}</ref><ref name="ods">{{Cite web | url=https://ods.od.nih.gov/factsheets/Choline-HealthProfessional/|title=Choline |publisher=Office of Dietary Supplements, US National Institutes of Health|date=2 June 2022|accessdate=31 October 2024 }}</ref> Choline forms various [[Salt (chemistry)|salts]], such as [[choline chloride]] and [[choline bitartrate]]. An [[essential nutrient]] for animals, it is a structural component of [[phospholipid]]s and [[cell membrane]]s.<ref name=lpi/><ref name=ods/>

Choline is used to synthesize [[acetylcholine]], a [[neurotransmitter]] involved in muscle control and numerous functions of the nervous system.<ref name=lpi/><ref name=ods/> Choline is involved in early development of the brain, [[gene expression]], cell membrane [[Signaling peptide receptor|signaling]], and brain metabolism.<ref name=ods/>

Although humans synthesize choline in the [[liver]], the amount produced naturally is insufficient to meet cellular functions, requiring that some choline be obtained from foods or [[dietary supplement]]s.<ref name=ods/> Foods rich in choline include meats, poultry, eggs, and other animal-based products, [[cruciferous vegetables]], beans, nuts, and [[whole grain]]s.<ref name=ods/> Choline is present in breast milk and is commonly added as an [[food additive|ingredient]] to [[baby food]]s.<ref name=ods/>