{"id":551,"date":"2022-10-04T18:31:40","date_gmt":"2022-10-04T16:31:40","guid":{"rendered":"https:\/\/modafinil.pl\/sklep\/cdp-choline-%e2%89%a5-99-1000mg\/"},"modified":"2026-09-30T07:25:09","modified_gmt":"2026-09-30T05:25:09","slug":"cdp-choline-%e2%89%a5-99-1000mg","status":"publish","type":"product","link":"https:\/\/modafinil.pl\/en\/sklep\/cdp-choline-%e2%89%a5-99-1000mg\/","title":{"rendered":"CDP-choline \/ Citicoline (CAS 987-78-0) \u2014 laboratory reagent 1000 mg, purity \u2265 99%"},"content":{"rendered":"

Cytidine 5\u2032-diphosphocholine (CDP-choline)<\/strong>, crystalline powder, 1000 mg pack. Material intended exclusively for laboratory and analytical in vitro research<\/strong>. This product is not intended for human or animal consumption<\/strong>; it is not a medicinal product, food supplement, foodstuff or cosmetic.<\/p>\n

Three different entities that must not be confused<\/h2>\n

The same chemical name circulates in three entirely different contexts, with a different legal status, different quality control and a different intended use. Separating them is as important here as for every other item in our catalogue:<\/p>\n\n\n\n\n\n\n\n
Separating the layers: substance \u2014 medicinal product \u2014 reagent<\/caption>\n
Entity<\/th>\nWhat it is<\/th>\nWhat it concerns<\/th>\n<\/tr>\n<\/thead>\n
Chemical substance
citicoline, CAS 987-78-0<\/th>\n		A chemical concept \u2014 a nucleotide coenzyme of defined structure. In itself it is neither a medicine nor a reagent; its status is conferred by the form in which it has been manufactured and authorised.<\/td>\nchemistry, biochemistry, substance registries<\/td>\n<\/tr>\n
Medicinal product
a preparation with a trade name such as Nicholin (other trade names depend on the country of registration)<\/th>\n		A pharmaceutical preparation: a defined pharmaceutical form and strength, GMP manufacturing, registration documentation, pharmacovigilance. It is precisely this entity that the clinical studies involving humans<\/strong> cited in the literature concern.<\/td>\nthe clinical studies concerned this entity<\/strong><\/td>\n<\/tr>\n
Chemical reagent
material offered here<\/th>\n		Material for laboratory and analytical work. It does not have, and cannot have, authorisation for use in humans or animals<\/strong> \u2014 it has no pharmaceutical form or medicinal-product documentation.<\/td>\nanalytics, chemistry, reference standards<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

The consequence is unambiguous.<\/strong> The study results cited further on this page were obtained either using a registered medicinal product or a preparation given to volunteers in a clinical study<\/strong> (human data), or using the substance administered to laboratory animals under controlled experimental conditions<\/strong> (preclinical studies), or they concern solely the chemistry and biochemistry of the molecule<\/strong> (synthesis, crystallisation, enzymatic mechanism) without it being administered to anyone. None of these studies was conducted using the analytical reagent<\/strong>, and none of their results transfers to the material offered.<\/p>\n

Reagent identification sheet<\/h2>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
Registry data and identifiers \u2014 CDP-choline<\/caption>\n
Systematic name (IUPAC)<\/th>\n[[(2R<\/em>,3S<\/em>,4R<\/em>,5R<\/em>)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 2-(trimethylazaniumyl)ethyl phosphate<\/td>\n<\/tr>\n
Common name \/ INN<\/th>\nciticoline (cytykolina, CDP-choline)<\/td>\n<\/tr>\n
CAS number<\/th>\n987-78-0<\/td>\n<\/tr>\n
Molecular formula<\/th>\nC14<\/sub>H26<\/sub>N4<\/sub>O11<\/sub>P2<\/sub><\/td>\n<\/tr>\n
Molar mass<\/th>\n488.32 g\u00b7mol\u22121<\/sup><\/td>\n<\/tr>\n
Monoisotopic mass<\/th>\n488.1073 Da<\/td>\n<\/tr>\n
InChIKey<\/th>\nRZZPDXZPRHQOCG-OJAKKHQRSA-N<\/td>\n<\/tr>\n
SMILES (isomeric)<\/th>\nC[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<\/td>\n<\/tr>\n
PubChem CID<\/th>\n13804<\/a><\/td>\n<\/tr>\n
ChEMBL<\/th>\nCHEMBL5903940<\/td>\n<\/tr>\n
Form<\/th>\ncrystalline powder, white to off-white<\/td>\n<\/tr>\n
Purity<\/th>\n\u2265 99%<\/td>\n<\/tr>\n
Intended use<\/th>\nresearch reagent \u2014 not for human or animal consumption<\/strong><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Lineage of the molecule: a coenzyme, not a drug candidate<\/h2>\n

CDP-choline is an exception in our catalogue in one respect: it did not originate as a product of medicinal synthesis designed for a specific therapeutic target. It is a natural nucleotide coenzyme<\/strong>, present in every living cell, which only later became a subject of interest for pharmacology.<\/p>\n

From coenzyme chemistry to a molecule on the laboratory shelf<\/h3>\n

The starting point was the work of Eugene P. Kennedy, who in the mid-1950s described the chemical synthesis of cytidine 5\u2032-diphosphocholine and the related cytidine 5\u2032-diphosphoethanolamine, showing that the cell \u201cactivates\u201d choline for incorporation into membrane phospholipids via a cytidine nucleotide \u2014 a mechanism analogous to the activation of glucose by UDP in other metabolic pathways [1<\/a>]. This phosphatidylcholine biosynthetic pathway now bears his name \u2014 the Kennedy pathway (CDP-choline pathway)<\/strong>.<\/p>\n

Confirmation in nature: crystallisation from yeast<\/h3>\n

In the same year a paper appeared confirming that the structure proposed by Kennedy was not merely a theoretical construct: Berger and Gimenez crystallised cytidine 5\u2032-diphosphocholine directly from yeast, proving that it is a compound genuinely produced by the cell and not merely a product of chemical synthesis [2<\/a>].<\/p>\n

A chemical curiosity: could such a coenzyme have formed without enzymes?<\/h3>\n

Because CDP-choline belongs to the family of nucleotide-diphosphate coenzymes (alongside, for example, UDP-glucose), it has also become an object of interest in prebiotic chemistry. A 1987 paper by Mar, Dworkin and Or\u00f3 showed that compounds of this type can form non-enzymatically<\/strong> under conditions resembling the early Earth \u2014 an argument in the discussion on the origin of cellular metabolism, which, however, has no connection whatsoever with the use of the reagent offered [3<\/a>].<\/p>\n

Where the registered medicinal product came from<\/h3>\n

Pharmacological interest in this molecule stems directly from its biochemical role: since CDP-choline is an obligatory intermediate in phosphatidylcholine synthesis, and the rate-limiting step of this synthesis responds to the cell\u2019s demand for membrane phospholipids, its exogenous administration became a subject of research as a means of supporting the rebuilding of cell membranes after nerve tissue injury. On this basis, over the following decades, medicinal products<\/strong> were registered under various trade names in selected countries \u2014 it was these, and not the analytical reagent, that were the subject of the clinical studies involving humans cited below.<\/p>\n

Timeline<\/h2>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
Timeline: from the discovery of the coenzyme to modern structural biology<\/caption>\n
1956<\/th>\nchemical synthesis of CDP-choline and CDP-ethanolamine by Kennedy \u2014 description of the choline activation pathway [1<\/a>]<\/td>\n<\/tr>\n
1956<\/th>\ncrystallisation of CDP-choline from yeast \u2014 confirmation of its natural occurrence [2<\/a>]<\/td>\n<\/tr>\n
1970s\u20131980s<\/th>\ndevelopment of pharmaceutical preparations based on this molecule; registrations as a medicinal product in selected European and Asian countries<\/td>\n<\/tr>\n
1987<\/th>\ndemonstration of the non-enzymatic (prebiotic) synthesis of nucleotide-diphosphate coenzymes, including CDP-choline [3<\/a>]<\/td>\n<\/tr>\n
1996<\/th>\nstudy of histological and behavioural efficacy in an animal model of focal ischaemia [4<\/a>]<\/td>\n<\/tr>\n
1999<\/th>\ndevelopment of a method for separating choline metabolites without HPLC \u2014 two-dimensional electrophoresis and TLC [5<\/a>]<\/td>\n<\/tr>\n
2001<\/th>\ndescription of the role of the CDP-choline pathway in phosphatidylcholine turnover in a yeast model [6<\/a>]<\/td>\n<\/tr>\n
2002<\/th>\nin vivo phosphorus magnetic resonance spectroscopy (31<\/sup>P-MRS) study in healthy older volunteers [7<\/a>]<\/td>\n<\/tr>\n
2004<\/th>\ndescription of elevated erythrocyte CDP-choline levels in a rare transfusion-independent anaemia [8<\/a>]<\/td>\n<\/tr>\n
2005<\/th>\nstudy of the neuroprotection mechanism in an animal model of cerebral ischaemia \u2014 glutamate transport [9<\/a>]<\/td>\n<\/tr>\n
2011<\/th>\npharmacological and clinical review concerning the medicinal product [10<\/a>]<\/td>\n<\/tr>\n
2012<\/th>\nmulticentre phase III clinical trial (COBRIT) published in JAMA<\/em> [11<\/a>]<\/td>\n<\/tr>\n
2013<\/th>\ndescription of the mechanism of the enzyme CTP:phosphocholine cytidylyltransferase \u2014 the key enzyme of the Kennedy pathway [12<\/a>]<\/td>\n<\/tr>\n
2018<\/th>\ndevelopment of a one-pot enzymatic synthesis of CDP-choline under industrial conditions [13<\/a>]<\/td>\n<\/tr>\n
2020<\/th>\nreview of genetic diseases associated with disorders of the Kennedy pathway [14<\/a>]<\/td>\n<\/tr>\n
2024<\/th>\nthe most recent neuroprotection study in an animal model of acute cerebral ischaemia [15<\/a>]<\/td>\n<\/tr>\n
2025<\/th>\nstructural basis of catalysis by eukaryotic choline-phosphotransferase \u2014 the enzyme of the final step of the pathway [16<\/a>]<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Chemistry: a nucleotide coenzyme and extreme polarity<\/h2>\n

CDP-choline belongs to an entirely different chemical family from most reagents in our catalogue. Instead of a lipophilic aromatic skeleton, here we have a diphosphate nucleotide<\/strong>: a cytosine ring linked to ribofuranose, which in turn is linked \u2014 via a diphosphate bridge \u2014 to choline.<\/p>\n

Four stereogenic centres of the ribose ring<\/h3>\n

Unlike our reagents based on a single stereogenic centre (sulfur in modafinil) or lacking one altogether (the adamantane cage of bromantan), CDP-choline has four defined stereogenic centres<\/strong> \u2014 the (2R<\/em>,3S<\/em>,4R<\/em>,5R<\/em>) configuration of the oxolane ring, inherited from the natural D-ribose that forms part of cytidine. This is not a mixture that needs to be separated \u2014 it is a single, unambiguously defined stereoisomer, as found in natural cellular metabolism.<\/p>\n

An inner salt: positive nitrogen, negative phosphate<\/h3>\n

The molecule is an inner salt (zwitterion)<\/strong>: the quaternary nitrogen atom of choline carries a permanent positive charge, and one of the oxygens of the diphosphate bridge carries a negative charge. Both charges are present simultaneously, irrespective of the pH of the solution, which distinguishes this molecule from the other reagents in the catalogue, which are electrically neutral under physiological conditions.<\/p>\n

What the two phosphorus atoms reveal<\/h3>\n

The diphosphate bridge means the presence of two non-equivalent phosphorus atoms<\/strong>. Phosphorus-31 is an isotope of 100% natural abundance with a nuclear spin of \u00bd, which makes it a convenient nucleus for NMR spectroscopy. In the 31<\/sup>P NMR spectrum such a structure gives two distinct signals, coupled to each other through the P\u2013O\u2013P linkage \u2014 a signature analogous to that used in in vivo studies by 31<\/sup>P-MRS, which was applied in healthy volunteers to observe brain phospholipid metabolism after administration of the pharmaceutical preparation [7<\/a>].<\/p>\n\n\n\n\n\n\n\n\n\n\n
Physicochemical characteristics and their analytical significance<\/caption>\n
Parameter<\/th>\nValue<\/th>\nImplication<\/th>\n<\/tr>\n<\/thead>\n
Partition coefficient (XLogP)<\/th>\n\u2248 \u22124<\/td>\nextremely hydrophilic \u2014 the opposite of the lipophilic stimulants in this catalogue<\/td>\n<\/tr>\n
Topological polar surface area (TPSA)<\/th>\n214 \u00c52<\/sup><\/td>\none of the highest in the catalogue \u2014 a consequence of the two phosphate groups<\/td>\n<\/tr>\n
Hydrogen bond donors<\/th>\n4<\/td>\nribose hydroxyl groups and phosphate groups<\/td>\n<\/tr>\n
Hydrogen bond acceptors<\/th>\n11<\/td>\nphosphate, hydroxyl and ring oxygens<\/td>\n<\/tr>\n
Rotatable bonds<\/th>\n10<\/td>\nflexible phosphate\u2013choline chain<\/td>\n<\/tr>\n
Solubility<\/th>\nvery good in water; negligible in non-polar solvents<\/td>\nstock solutions are prepared in water, not in DMSO or methanol<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

The extreme polarity has a direct methodological consequence: classical reversed-phase chromatography (RP-HPLC) in a standard set-up retains this molecule poorly \u2014 it elutes close to the column dead volume. In practice, ion-pair chromatography, HILIC or non-chromatographic methods are used \u2014 hence the analytical literature on this molecule features electrophoresis, thin-layer chromatography and spectroscopic methods side by side, not only a classical RP-HPLC gradient [5<\/a>].<\/p>\n

Nomenclature and synonyms<\/h2>\n