{"Abbreviation":[],"Adverse Effects":"Dermatotoxin - Skin burns.","Aliases":["Choline","Choline ion","Bilineurine","62-49-7","Choline cation","2-Hydroxy-N,N,N-trimethylethanaminium","Cholinum","Ethanaminium, 2-hydroxy-N,N,N-trimethyl-","(2-Hydroxyethyl)trimethylammonium","trimethylethanolamine","vitamin J","N-trimethylethanolamine","(2-hydroxyethyl)trimethylazanium","N,N,N-trimethylethanol-ammonium","N91BDP6H0X","Chebi:15354","Dtxsid8043789","Gabazolamine","Gaboxetine","Sentroxatine","Sentrazolam AM","Citrate, Choline","Choline O Sulfate","Gabazolamine-0.5","O-Sulfate, Choline","Sentraflox AM-10","Sentralopram AM-10","Alprazolam, choline","Dtxcid6023789","2-hydroxyethyl-trimethyl-ammonium","Citalopram hydrobromide, choline","Fluoxetine hydrochloride, choline","200-535-1","CCRIS 5847","AI3-24208","Brn 1736748","(β-hydroxyethyl)trimethylammonium","CHEMBL920","2-hydroxy-N,N,N-trimethyl-ethanaminium","Bilineurine; Choline cation; Choline ion; Nanoveson C; Vitamin J","CHT","NSC402838","Ncgc00015219-03","Einecs 200-535-1","Unii-n91bdp6h0x","2-hydroxyethyl(trimethyl)ammonium","1oba","2reg","3ppq","Nanoveson c","Spectrum_000258","2ha3","3r6u","Ethanaminium,2-hydroxy-N,N,N-trimethyl-","Spectrum2_001938","Spectrum4_000867","Spectrum5_001579","Lopac-C-1754","bmse000285","bmse000953","bmse001003","Epitope ID:116046","Schembl3142","Lopac0_000180","KBioGR_001533","KBioSS_000738","3-04-00-00651","DivK1c_000107","N,N,N-trimethylethanolammonium","SPBio_001975","GTPL4551","Schembl1316669","KBio1_000107","KBio2_000738","KBio2_003306","KBio2_005874","NSC6393","Ninds_000107","(2-Hydroxyethyl)trimethyl ammonium","mono-2-hydroxyethyltrimethylammonium","NSC-6393","BBL005532","Bdbm50026220","STL137772","Akos005721137","2-Hydroxyethyl)trimethylammonium","CCG-204275","DB00122","Idi1_000107","Ncgc00015219-01","Ncgc00015219-02","Ncgc00015219-04","Ncgc00015219-07","Ncgc00015219-10","Ncgc00162082-01","Carbachol impurity a","Sbi-0050168.p003","2-Hydroxy-N,N,N-trimethylammonium chloride","DB-186977","NS00006125","(β-Hydroxyethyl)trimethylammonium","C00114","D07690","Ab00053822_02","Q193166","Acetylcholine chloride impurity a","Brd-k77300776-001-01-7","Brd-k77300776-001-02-5","InChI=1/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+"],"CAS":"62-49-7","Chemical Classes":"Biological Agents -\u003e Vitamins and Derivatives","ChemicalClasses":[],"Chirality":"achiral","Drug Indication":"For nutritional supplementation, also for treating dietary shortage or imbalance","Esters":[],"European Community (EC) Number":"200-535-1","Formating":[],"HMDB ID":"HMDB0000097","HeavyAtomCount":7,"IUPACName":"2-hydroxyethyl(trimethyl)azanium","InChI":"InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1","InChIKey":"OEYIOHPDSNJKLS-UHFFFAOYSA-N","MeSH Pharmacological Classification":"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.","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.","Melting Point":"244-247 °C (as chloride salt)","Metabolism/Metabolites":"Choline has known human metabolites that include Trimethylazanium and acetaldehyde.","MolecularFormula":"C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eNO+","MolecularWeight":"104.17 g/mol","Pharmacodynamics":"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.","Physical Description":"50% Aqueous solution: Dark brown cloudy liquid; [Sigma-Aldrich MSDS]","PubChemId":305,"Record Description":["LiverTox|HDS: Nutritional Sup|Vitamins|Vitamin B"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"5679","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Choline","Name":"Choline","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q193166","Name":"Choline","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00122","Name":"Choline","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/305","Name":"Choline","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=62-49-7","Name":"Choline","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0000097","Name":"Choline","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C00114","Name":"Choline","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/N91BDP6H0X","Name":"Choline","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID8043789","Name":"Choline","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 305, Choline. Accessed January 15, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/305\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/305\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Choline. UNII: N91BDP6H0X. Global Substance Registration System. Accessed January 15, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/N91BDP6H0X\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/N91BDP6H0X\u003c/a\u003e"],"SMILES":"C[N+](C)(C)CCO","SaltData":[{"AcidCount":1,"Amine":"Choline","AmineCount":1,"Formula":"O=C(O)c1ccccc1O","Name":"salicylate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 130.425 51.887\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h131v52H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M16.15 41.248v-11.39M16.15 21.791V10.768M12.809 26.008H.91M20.777 26.008H31.39M31.39 26.008l7.62-13.198M39.01 12.81h11.581\" 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