Citicoline

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Citicoline

Systematic (IUPAC) name
5'-O-[hydroxy({hydroxy[2-(trimethylammonio)ethoxy] phosphoryl}oxy)phosphoryl]cytidine
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	987-78-0 33818-15-4
ATC code	N06BX06
PubChem	CID 13805
ChemSpider	16736209^Y
UNII	536BQ2JVC7^Y
KEGG	D00057^Y
Synonyms	Cytidine diphosphate choline
Chemical data
Formula	C₁₄H₂₇N₄O₁₁P₂⁺
Mol. mass	489.332 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C12H22N4O11P2/c1-16(2,3)26-29(22,23)27-28(20,21)24-6-7-9(17)10(18)11(25-7)15-5-4-8(13)14-12(15)19/h4-5,7,9-11,17-18H,6H2,1-3H3,(H3-,13,14,19,20,21,22,23)/t7-,9-,10-,11-/m1/s1^Y Key:OPDHNBAEGPICKZ-QCNRFFRDSA-N^Y
Y(what is this?) (verify)

Citicoline (INN), also known as cytidine diphosphate-choline (CDP-Choline) & cytidine 5'-diphosphocholine is a psychostimulant/nootropic. It is an intermediate in the generation of phosphatidylcholine from choline. Sold in over 70 countries under a variety of brand names: Ceraxon, Cognizin, NeurAxon, Somazina etc.

Studies suggest that CDP-choline supplements increase dopamine receptor densities,^[1] and suggest that CDP-choline supplementation can ameliorate memory impairment caused by environmental conditions.^[2] Preliminary research has found that citicoline supplements help improve focus and mental energy and may possibly be useful in the treatment of attention deficit disorder.^[3]^[4] Citicoline has also been shown to elevate ACTH independent of CRH levels and to amplify the release of other HPA axis hormones such as LH, FSH, GH and TSH in response to hypothalamic releasing factors.^[5] These effects on HPA hormone levels may be beneficial for some individuals but, may have undesirable effects in those with medical conditions featuring ACTH or cortisol hypersecretion including, but not limited to, PCOS, type II diabetes and major depressive disorder.^[6]^[7]

[edit] See also

[edit] References

^ Giménez R, Raïch J, Aguilar J (November 1991). "Changes in brain striatum dopamine and acetylcholine receptors induced by chronic CDP-choline treatment of aging mice". British Journal of Pharmacology 104 (3): 575–8. PMC 1908237. PMID 1839138. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1908237.
^ Teather LA, Wurtman RJ (2005). "Dietary CDP-choline supplementation prevents memory impairment caused by impoverished environmental conditions in rats". Learning & Memory 12 (1): 39–43. doi:10.1101/lm.83905. PMC 548494. PMID 15647594. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=548494.
^ "Supplement naturally boosts ageing brain power". Sydney Morning Herald. 2008-02-25. http://www.smh.com.au/articles/2008/02/24/1203788130776.html. Retrieved 2009-07-28.
^ Silveri MM, Dikan J, Ross AJ, et al. (November 2008). "Citicoline enhances frontal lobe bioenergetics as measured by phosphorus magnetic resonance spectroscopy". NMR in Biomedicine 21 (10): 1066–75. doi:10.1002/nbm.1281. PMID 18816480.
^ Cavun S, Savci V (October 2004). "CDP-choline increases plasma ACTH and potentiates the stimulated release of GH, TSH and LH: the cholinergic involvement". Fundamental & Clinical Pharmacology 18 (5): 513–23. doi:10.1111/j.1472-8206.2004.00272.x. PMID 15482372.
^ Benson S, Arck PC, Tan S, et al. (June 2009). "Disturbed stress responses in women with polycystic ovary syndrome". Psychoneuroendocrinology 34 (5): 727–35. doi:10.1016/j.psyneuen.2008.12.001. PMID 19150179.
^ Florio P, Zatelli MC, Reis FM, degli Uberti EC, Petraglia F (2007). "Corticotropin releasing hormone: a diagnostic marker for behavioral and reproductive disorders?". Frontiers in Bioscience 12: 551–60. doi:10.2741/2081. PMID 17127316.

v · d · eDietary supplements

Types	Amino acids • Bodybuilding supplement • Energy drink • Energy bar • Fatty acids • Herbal Supplements • Minerals • Prebiotics • Probiotics (Lactobacillus, Bifidobacterium) • Protein bar • Vitamins

Vitamins and "minerals" (chemical elements)	Retinol (Vitamin A) • B vitamins: Thiamine (B₁) • Riboflavin (B₂) • Niacin (B₃) • Pantothenic acid (B₅) • Pyridoxine (B₆) • Biotin (B₇) • Folic acid (B₉) • Cyanocobalamin (B₁₂) • Ascorbic acid (Vitamin C) • Ergocalciferol and Cholecalciferol (Vitamin D) • Tocopherol (Vitamin E) • Naphthoquinone (Vitamin K) • Calcium • Choline • Chromium • Cobalt • Copper • Fluorine • Iodine • Iron • Magnesium • Manganese • Molybdenum • Phosphorus • Potassium • Selenium • Sodium • Sulfur • Zinc

Other common ingredients	AAKG • Carnitine • Chondroitin sulfate • Cod liver oil • Copper gluconate • Creatine/Creatine supplements • Dietary fiber • Echinacea • Elemental calcium • Ephedra • Fish oil • Folic acid • Ginseng • Glucosamine • Glutamine • Grape seed extract • Guarana • Iron supplements • Japanese Honeysuckle • Krill oil • Lingzhi • Linseed oil • Lipoic acid • Milk thistle • Melatonin • Red yeast rice • Royal jelly • Saw palmetto • Spirulina • St John's wort • Taurine • Wheatgrass • Wolfberry • Yohimbine • Zinc gluconate

Related articles	Codex Alimentarius • Enzyte • Hadacol • Nutraceutical • Multivitamin • Nutrition

v · d · eNootropics (N06B)

Acetylcholinesterases	Donepezil • Galantamine • Huperzine A (Huperzia Serrata) • Ladostigil • Rivastigmine • Tacrine

Ampakines	CX-516 • CX-546 • CX-614 • CX-691 • CX-717 • IDRA-21 • LY-404,187 • LY-503,430 • PEPA • Sunifiram • Unifiram

D₁ Agonists	6-Br-APB • A-77636 • Dihydrexidine • Dinapsoline • Doxanthrine • SKF-81297

Eugeroics	Adrafinil • Armodafinil • Modafinil

GABA_A α₅ Inverse Agonists	α5IA • L-655,708 • PWZ-029 • Suritozole • TB-21007 • ZK-93426

H₃ Antagonists	A-349,821 • ABT-239 • Ciproxifan • GSK-189,254

mACh Agonists	Alvameline • Arecoline • Cevimeline • CI-1017 • Milameline • Sabcomeline • Talsaclidine • Tazomeline • Xanomeline

nACh Agonists	AR-R17779 • Ispronicline • Nicotine • PNU-282,987 • SSR-180,711 • WAY-317,538

Racetams	Aniracetam • Brivaracetam • Coluracetam • Etiracetam • Fasoracetam • Levetiracetam • Nebracetam • Nefiracetam • Oxiracetam • Phenylpiracetam • Piracetam • Pramiracetam • Rolziracetam • Seletracetam

Others	Acetylcarnitine • Adafenoxate • Bifemelane • Bilobalide (Ginkgo Biloba) • Carbenoxolone • Cerlapirdine • Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine • Ensaculin • Fipexide • Idebenone • Indeloxazine • Latrepirdine • Leteprinim • Linopirdine • Meclofenoxate • Nizofenone • Pirisudanol • Pyritinol • S-17092 • Sulbutiamine • Taltirelin • Teniloxazine • Tricyanoaminopropene • Vinpocetine

Cholinergics

Receptor ligands

mAChR	Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine • Suberylcholine • Talsaclidine • Tazomeline • Thiopilocarpine • Vedaclidine • VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-796 Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide • Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium bromide • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • PD-0298029 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium bromide • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine, triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine, etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc)

nAChR	Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • Anatoxin-a • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • WAY-317,538 • XY-4083 Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid • Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium • Xenon

Reuptake inhibitors

Plasmalemmal

CHT Inhibitors

Hemicholinium-3 (Hemicholine; HC3) • Triethylcholine

VAChT Inhibitors

ChAT inhibitors

1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • N,N-Dimethylaminoethylacrylate • N,N-Dimethylaminoethylchloroacetate

Catabolism

AChE inhibitors	Reversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi)

BChE inhibitors	Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.

Others

Precursors	Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE, deanol) • Glycerophosphocholine • Meclofenoxate (Centrophenoxine) • Phosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine • Pirisudanol

Cofactors	Acetic acid • Acetylcarnitine • Acetyl-coA • Vitamin B₅ (Pantethine, Pantetheine, Panthenol)

Others	Acetylcholine releasing agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime • Obidoxime • Pralidoxime