| Revision as of 17:05, 30 October 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added SMILES, CSID, (Std)InChI & (Std)InChIKey← Previous edit |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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| verifiedrevid = 448003868 |
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{{Infobox drug |
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| IUPAC_name = 2-trimethylazaniumylethyl phosphate |
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| Verifiedfields = changed |
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| image = Choline alfoscerate.svg |
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| Watchedfields = changed |
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| verifiedrevid = 458279808 |
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| IUPAC_name = 2-trimethylazaniumylethyl phosphate <!-- see www.fda.gov/ucm/groups/fdagov-public/@fdagov-foods-gen/documents/document/ucm299330.pdf#page=12 --> |
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| image = L-alpha-GPC Structural Formula V.1.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 28319-77-9 |
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| CAS_number = 28319-77-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 60M22SGW66 |
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| ATC_prefix = N07 |
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| ATC_prefix = N07 |
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| ATC_suffix = AX02 |
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| ATC_suffix = AX02 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| PubChem = 71920 |
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| ChEBI = 55397 |
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| PubChem = 657272 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 571409 |
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| ChemSpiderID = 571409 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1567463 |
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| smiles = P(=O)(OC(O)CO)OCC(C)(C)C |
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| smiles = P(=O)(OC(O)CO)OCC(C)(C)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/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 |
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| InChIKey = SUHOQUVVVLNYQR-MRVPVSSYBR |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SUHOQUVVVLNYQR-MRVPVSSYSA-N |
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| StdInChIKey = SUHOQUVVVLNYQR-MRVPVSSYSA-N |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=8 | H=20 | N=1 | O=6 | P=1 |
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| C=8 | H=20 | N=1 | O=6 | P=1 |
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| molecular_weight = 257.221 g/mol |
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}} |
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}} |
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'''L-Alpha Glycerylphosphorylcholine''' ('''Alpha GPC''', '''choline alfoscerate''') is a natural ] compound found in the brain and in milk. It is also a ] ] precursor<ref name="pmid12637119">{{cite journal |author=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=Clin Ther |volume=25 |issue=1 |pages=178–93 |year=2003 |month=January |pmid=12637119 |doi= 10.1016/S0149-2918(03)90023-3|url=http://linkinghub.elsevier.com/retrieve/pii/S0149291803900233}}</ref> which may have potential for the treatment of ] and is used as a ] ] to enhance memory and cognition. |
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'''<small>L</small>-α-Glycerophosphorylcholine''' ('''alpha-GPC''', '''choline alfoscerate''', '''''sn''-glycero-3-phosphocholine''') is a natural ] compound found in the brain. It is also a ] ] 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 ]<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 }} |
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</ref> and other ]s.<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> |
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Alpha-GPC rapidly delivers ] to the brain across the ] and is a biosynthetic precursor of ].<ref name="Parnetti" /> It is a non-prescription drug in most countries. The ] determined that intake of no more than 196.2 mg/person/day is considered ] (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> |
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Alpha GPC rapidly delivers ] to the brain across the blood-brain barrier and is a biosynthetic precursor of the acetylcholine neurotransmitter.<ref>{{cite journal |
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| last =Parnetti |
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| first = Lucilla |
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| coauthors = et al. |
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| year = 2007 |
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| title = Cholinergic precursors in the treatment of cognitive impairment of vascular origin: Ineffective approaches or need for re-evaluation? |
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| journal = Journal of the Neurological Sciences |
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| volume = 257 |
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| pages = 264–9 |
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| pmid = 17331541 |
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| issue =1–2 |
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| doi =10.1016/j.jns.2007.01.043 |
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}} |
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</ref> Alpha GPC is derived from highly purified soy ]. |
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== Production == |
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Studies have investigated its efficacy for cognitive disorders including stroke and ]. 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.<ref>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.</ref> |
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Industrially, alpha-GPC is produced by the chemical or enzymatic deacylation of ] enriched soya ] followed by ]. Alpha-GPC may also be derived in small amounts from highly purified soy ] 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> |
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== Safety == |
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Commonly used doses are 300-1,200 mg daily. |
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Alpha-GPC metabolizes to ] in the gastrointestinal tract, which has implications for cardiovascular health. In one study, risk of stroke over a ten-year period was increased by about 40% in users of alpha-GPC.<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 | volume = 4 | issue = 11 | pages = e2136008 | date = November 2021 | pmid = 34817582 | pmc = 8613599 | doi = 10.1001/jamanetworkopen.2021.36008 }}</ref> |
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== References == |
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== References == |
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{{Reflist|2}} |
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{{Reflist|2}} |
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== External links == |
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{{Dietary_supplements}} |
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{{Dietary_supplements}} |
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{{Nootropics}} |
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{{Acetylcholine receptor modulators}} |
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{{Cholinergics}} |
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{{DEFAULTSORT:Alpha-Gpc}} |
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{{DEFAULTSORT:Alpha-Gpc}} |
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