Citicoline

Base Information

• Chemical Name: Citicoline
• CAS No.: 987-78-0
• Molecular Formula: C14H26N4O11P2
• Molecular Weight: 488.328
• Hs Code.: 2942000000
• European Community (EC) Number: 213-580-7
• DSSTox Substance ID: DTXSID9048431
• Wikipedia: Citicoline
• Wikidata: Q28529682
• NCI Thesaurus Code: C96743
• Metabolomics Workbench ID: 37783
• Mol file: 987-78-0.mol

Synonyms:5'-Diphosphocholine, Cytidine;CDP Choline;Choline, CDP;Choline, Cytidine Diphosphate;Cidifos;Citicholine;Citicoline;Cyticholine;Cytidine 5' Diphosphocholine;Cytidine 5'-Diphosphocholine;Cytidine Diphosphate Choline;Diphosphate Choline, Cytidine

Chemical Property of Citicoline

Chemical Property:

• Appearance/Colour: White powder
• Boiling Point: 851.4°C at 760 mmHg
• PKA: 4.4(at 25℃)
• PSA: 235.34000
• LogP: -0.57910
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Water (Sparingly)
• XLogP3: -4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 488.10733165
• Heavy Atom Count: 31
• Complexity: 821

Purity/Quality:

Cytidine5''-Diphosphocholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OCC1C(C(C(O1)N2C=CC(=NC2=O)N)O)O
• Isomeric SMILES: C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O
• Recent ClinicalTrials: Clinical Medication Development for Bipolar Disorder and Alcohol Use Disorders
• Recent EU Clinical Trials: CITICOLINA EN LA EVOLUCIóN DE LA LEUCOARAIOSIS A MEDIO-LARGO PLAZO. ESTUDIO ALEATORIZADO Y CONTROLADO CON PLACEBO
• Description: Citicoline whose chemical name choline cytosine nucleoside-5'-diphosphate monosodium salt, is a precursor for lecithin biosynthesis, and when brain function declines, the content of lecithin in brain tissue is significantly reduced.
• Uses: Cytidine 5'-Diphosphocholine is used as antidepressant, 5HT uptake inhibitor.
• Therapeutic Function: Cerebral circulation stimulant

Technology Process of Citicoline

There total 11 articles about Citicoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

C11H17N3O11P2 + trimethylamine (75-50-3) → citicoline (987-78-0)

Guidance literature:

In ethanol; at 20 ℃; for 10h;

Reference yield: 85.0%

phosphorylcholine chloride, calcium salt (4826-71-5) + cytidine 5'-monophosphate morpholidate (76742-17-1) → citicoline (987-78-0)

Guidance literature:

With sulfuric acid; In methanol; at 50 ℃; for 3h;

DOI:10.3184/174751916X14628025243831

Reference yield:

cytidine-5'-phosphodichloride (30784-94-2) + choline phosphate calcium salt → citicoline (987-78-0) + cytidine-5'-phosphodimorpholide (122450-01-5) + cytidine monophosphate (63-37-6,30811-80-4) + cytidine 5'-monophosphate morpholidate (76742-17-1)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1007/BF00764626

upstream raw materials:

trimethyl-(2-phosphono-ethyl)-ammonium

cytidine monophosphate

cytidine-5'-phosphodichloride

alpha-D-glucopyranose

Downstream raw materials:

2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine

cytidine 5'-diphosphocholine sodium salt

Refernces

• 1、 -. "Citicoline and synthetic method thereof". Paragraph 0014; 0016; 0019. . Retrieved 2016/10/24.
• 2、 Ghezal, Salma,Thomasson, Maggie S.,Lefebvre-Tournier, Isabelle,Périgaud, Christian,Macnaughtan, Megan A.,Roy, Béatrice. "CDP-Ethanolamine and CDP-Choline: One-pot synthesis and 31P NMR study". . p. 5306 - 5310. Retrieved 2015/01/16.