Alpha-GPC

Alpha-GPC

Systematic (IUPAC) name
[(2S)-2,3-dihydroxypropyl] 2-trimethylazaniumylethyl phosphate
Clinical data
Pregnancy cat.	?
Legal status	OTC
Identifiers
CAS number	28319-77-9^N
ATC code	N07AX02
PubChem	CID 71920
ChemSpider	571409^Y
ChEBI	CHEBI:55397^Y
Chemical data
Formula	C₈H₂₀N O₆P
Mol. mass	257.221 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m1/s1^Y Key:SUHOQUVVVLNYQR-MRVPVSSYSA-N^Y
N(what is this?) (verify)

L-Alpha Glycerylphosphorylcholine (Alpha GPC, choline alfoscerate) is a natural choline compound found in the brain and in milk. It is also a parasympathomimetic acetylcholine precursor^[1] which may have potential for the treatment of Alzheimer's disease and is used as a nootropic dietary supplement to enhance memory and cognition.

Alpha GPC rapidly delivers choline to the brain across the blood-brain barrier and is a biosynthetic precursor of the acetylcholine neurotransmitter.^[2] Alpha GPC is derived from highly purified soy lecithin.

Studies have investigated its efficacy for cognitive disorders including stroke and Alzheimer’s Disease. An Italian multicentre clinical trial on 2,044 patients suffering from recent stroke were supplied alpha-GPC in doses of 1,000 mg/day for 28 days and 400 mg three times per day for the five ensuing months. The trial confirmed the therapeutic role of alpha-GPC on the cognitive recovery of patients based on four measurement scales, three of which reached statistical significance.^[3]

Commonly used doses are 300-1,200 mg daily.

References

^ De Jesus Moreno Moreno M (January 2003). "Cognitive improvement in mild to moderate Alzheimer's dementia after treatment with the acetylcholine precursor choline alfoscerate: a multicenter, double-blind, randomized, placebo-controlled trial". Clin Ther 25 (1): 178–93. doi:10.1016/S0149-2918(03)90023-3. PMID 12637119. http://linkinghub.elsevier.com/retrieve/pii/S0149291803900233.
^ Parnetti, Lucilla; et al. (2007). "Cholinergic precursors in the treatment of cognitive impairment of vascular origin: Ineffective approaches or need for re-evaluation?". Journal of the Neurological Sciences 257 (1–2): 264–9. doi:10.1016/j.jns.2007.01.043. PMID 17331541.
^ Barbagallo Sangiorgi G, et al. "Alpha-Glycerophosphocholine in the mental recovery of cerebral ischemic attacks." An Italian multicenter clinical trial. Ann NY Acad Sci 1994; 717:253-69.

Dietary 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

Nootropics (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

Vesicular

VAChT Inhibitors	Vesamicol

Enzyme inhibitors

Anabolism

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