Glycerophosphorylcholine

{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 458279808 | IUPAC_name = [(2''R'')-2,3-Dihydroxypropyl] 2-trimethylazaniumylethyl phosphate  | image = L-alpha-GPC Structural Formula V.1.svg | image_class = skin-invert-image | image2 = AGPCTHREED.png | image_class2 = bg-transparent

| tradename = | pregnancy_AU =  | pregnancy_US =  | legal_AU =  | legal_CA =  | legal_UK =  | legal_US =  | legal_status = OTC

| CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 28319-77-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 60M22SGW66 | ATC_prefix = N07 | ATC_suffix = AX02 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 55397 | PubChem = 657272 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 571409 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1567463 | smiles = [O-]P(=O)(OC[C@H](O)CO)OCC[N+](C)(C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = SUHOQUVVVLNYQR-MRVPVSSYSA-N

| C = 8 | H = 20 | N = 1 | O = 6 | P = 1 }}

'''<small>L</small>-α-Glycerophosphorylcholine''' ('''alpha-GPC''', '''choline alfoscerate''', '''''sn''-glycero-3-phosphocholine''') is a natural choline compound found in the brain. It is also a parasympathomimetic acetylcholine precursor<ref name="pmid12637119">{{cite journal | vauthors = De Jesus Moreno Moreno M | title = 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 | journal = Clinical Therapeutics | volume = 25 | issue = 1 | pages = 178–93 | date = January 2003 | pmid = 12637119 | doi = 10.1016/S0149-2918(03)90023-3 }}</ref> which has been investigated for its potential for the treatment of Alzheimer's disease<ref name="Parnetti">{{cite journal | vauthors = Parnetti L, Mignini F, Tomassoni D, Traini E, Amenta F | title = Cholinergic precursors in the treatment of cognitive impairment of vascular origin: ineffective approaches or need for re-evaluation? | journal = Journal of the Neurological Sciences | volume = 257 | issue = 1–2 | pages = 264–9 | date = June 2007 | pmid = 17331541 | doi = 10.1016/j.jns.2007.01.043 | s2cid = 34661218 }} </ref> and other dementias.<ref name="Doggrell">{{cite journal | vauthors = Doggrell SA, Evans S | title = Treatment of dementia with neurotransmission modulation | journal = Expert Opinion on Investigational Drugs | volume = 12 | issue = 10 | pages = 1633–54 | date = October 2003 | pmid = 14519085 | doi = 10.1517/13543784.12.10.1633 | s2cid = 46175609 }}</ref>

Alpha-GPC rapidly delivers choline to the brain across the blood–brain barrier and is a biosynthetic precursor of acetylcholine.<ref name="Parnetti" /> It is a non-prescription drug in most countries. The FDA determined that intake of no more than 196.2 mg/person/day is considered generally recognized as safe (GRAS).<ref>{{cite web |url= https://www.accessdata.fda.gov/scripts/fcn/gras_notices/GRN000419.pdf | archive-url = https://web.archive.org/web/20131224102629/https://www.accessdata.fda.gov/scripts/fcn/gras_notices/GRN000419.pdf | archive-date = 24 December 2013 |title= Generally Recognized as Safe (GRAS) Determination for the Use of AlphaSize® Alpha-Glycerylphosphoryl Choline | date = 25 January 2012 | publisher = United States Food and Drug Administration }}</ref>

== Production == Industrially, alpha-GPC is produced by the chemical or enzymatic deacylation of phosphatidylcholine enriched soya phospholipids followed by chromatographic purification. Alpha-GPC may also be derived in small amounts from highly purified soy lecithin as well as from purified sunflower lecithin.<ref name="Traini_2013">{{cite journal | vauthors = Traini E, Bramanti V, Amenta F | title = Choline alphoscerate (alpha-glyceryl-phosphoryl-choline) an old choline- containing phospholipid with a still interesting profile as cognition enhancing agent | journal = Current Alzheimer Research | volume = 10 | issue = 10 | pages = 1070–9 | date = December 2013 | pmid = 24156263 | doi = 10.2174/15672050113106660173 }}</ref><ref name="Scapicchio_2013">{{cite journal | vauthors = Scapicchio PL | title = Revisiting choline alphoscerate profile: a new, perspective, role in dementia? | journal = The International Journal of Neuroscience | volume = 123 | issue = 7 | pages = 444–9 | date = July 2013 | pmid = 23387341 | doi = 10.3109/00207454.2013.765870 | url = }}</ref>

== Safety == A retrospective cohort study involving 12 million participants in South Korea found that α-GPC users had a higher risk of stroke (46 % higher). The authors suggested that one possible explanation is that dysbiosis may lead to α-GPC being metabolized into trimethylamine (TMA) in the gastrointestinal tract, and then to trimethylamine N-oxide (TMAO) in the liver, which has implications for cardiovascular health. However, they also noted that the study could be influenced by confounding variables, as α-GPC is often prescribed to individuals with preexisting health risks.<ref>{{cite journal | vauthors = Lee G, Choi S, Chang J, Choi D, Son JS, Kim K, Kim SM, Jeong S, Park SM | title = Association of L-α Glycerylphosphorylcholine With Subsequent Stroke Risk After 10 Years | journal = JAMA Network Open |issn=2574-3805 | volume = 4 | issue = 11 | pages = e2136008 | date = November 2021 | pmid = 34817582 | pmc = 8613599 | doi = 10.1001/jamanetworkopen.2021.36008 |doi-access=free |s2cid=244529061 }}</ref>

A later systematic review and meta-analysis criticized the statistical analysis of the South Korean cohort study, describing it as questionable and imprecise. The review concluded that α-GPC has a favorable safety and tolerability profile and is effective in improving cognitive function and daily living in patients with dementia disorders of neurological origin, adult-onset vascular dementia, and Alzheimer’s disease.<ref name="Sagaro2023">{{cite journal | vauthors = Sagaro GG, Traini E, Amenta F | title = Activity of Choline Alphoscerate on Adult-Onset Cognitive Dysfunctions: A Systematic Review and Meta-Analysis | journal = Journal of Alzheimer's Disease | volume = 92 | issue = 1 | pages = 59–70 | date = 2023-03-07 | pmid = 36683513 | pmc = 10041421 | doi = 10.3233/JAD-221189 | s2cid = 256104555 | doi-access = free }}</ref>

== References == {{Reflist|2}}

== External links == * [https://psychonautwiki.org/wiki/Alpha-GPC Alpha-GPC on PsychonautWiki] {{Dietary_supplements}}

Category:Cholinergics Category:Dietary supplements Category:Neurotransmitter precursors Category:Nutrition Category:Vitamins Category:Neuropharmacology Category:Glycerol esters