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Glycerophosphorylcholine

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(Redirected fromCholine alfoscerate)
Glycerophosphorylcholine
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • [(2R)-2,3-Dihydroxypropyl] 2-trimethylazaniumylethyl phosphate
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.044.496Edit this at Wikidata
Chemical and physical data
FormulaC8H20NO6P
Molar mass257.223g·mol−1
3D model (JSmol)
  • [O-]P(=O)(OC[C@H](O)CO)OCC[N+](C)(C)C
  • 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/s1checkY
  • Key:SUHOQUVVVLNYQR-MRVPVSSYSA-NcheckY
☒NcheckY(what is this?)(verify)

L-α-Glycerophosphorylcholine(alpha-GPC,choline alfoscerate,sn-glycero-3-phosphocholine) is a naturalcholinecompound found in the brain. It is also aparasympathomimeticacetylcholineprecursor[1]which has been investigated for its potential for the treatment ofAlzheimer's disease[2]and otherdementias.[3]

Alpha-GPC rapidly deliverscholineto the brain across theblood–brain barrierand is a biosynthetic precursor ofacetylcholine.[2]It is a non-prescription drug in most countries. TheFDAdetermined that intake of no more than 196.2 mg/person/day is consideredgenerally recognized as safe(GRAS).[4]

Production

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Industrially, alpha-GPC is produced by the chemical or enzymatic deacylation ofphosphatidylcholineenriched soyaphospholipidsfollowed bychromatographic purification.Alpha-GPC may also be derived in small amounts from highly purified soylecithinas well as from purified sunflower lecithin.[5][6]

Safety

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Alpha-GPC metabolizes totrimethylamine n-oxidein 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.[7]

References

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  1. ^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".Clinical Therapeutics.25(1): 178–93.doi:10.1016/S0149-2918(03)90023-3.PMID12637119.
  2. ^abParnetti L, Mignini F, Tomassoni D, Traini E, Amenta F (June 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.PMID17331541.S2CID34661218.
  3. ^Doggrell SA, Evans S (October 2003). "Treatment of dementia with neurotransmission modulation".Expert Opinion on Investigational Drugs.12(10): 1633–54.doi:10.1517/13543784.12.10.1633.PMID14519085.S2CID46175609.
  4. ^"Generally Recognized as Safe (GRAS) Determination for the Use of AlphaSize® Alpha-Glycerylphosphoryl Choline"(PDF).United States Food and Drug Administration. 25 January 2012. Archived fromthe original(PDF)on 24 December 2013.
  5. ^Traini E, Bramanti V, Amenta F (December 2013). "Choline alphoscerate (alpha-glyceryl-phosphoryl-choline) an old choline- containing phospholipid with a still interesting profile as cognition enhancing agent".Current Alzheimer Research.10(10): 1070–9.doi:10.2174/15672050113106660173.PMID24156263.
  6. ^Scapicchio PL (July 2013). "Revisiting choline alphoscerate profile: a new, perspective, role in dementia?".The International Journal of Neuroscience.123(7): 444–9.doi:10.3109/00207454.2013.765870.PMID23387341.
  7. ^Lee G, Choi S, Chang J, Choi D, Son JS, Kim K, et al. (November 2021)."Association of L-α Glycerylphosphorylcholine With Subsequent Stroke Risk After 10 Years".JAMA Network Open.4(11): e2136008.doi:10.1001/jamanetworkopen.2021.36008.PMC8613599.PMID34817582.
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