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Glycerophosphorylcholine

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(Redirected from Sn-Glycero-3-phosphocholine)

Glycerophosphorylcholine
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • [(2R)-2,3-Dihydroxypropyl] 2-trimethylazaniumylethyl phosphate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.044.496 Edit this at Wikidata
Chemical and physical data
FormulaC8H20NO6P
Molar mass257.223 g·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/s1 checkY
  • Key:SUHOQUVVVLNYQR-MRVPVSSYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

L-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[1] which has been investigated for its potential for the treatment of Alzheimer's disease[2] and other dementias.[3]

Alpha-GPC rapidly delivers choline to the brain across the blood–brain barrier and is a biosynthetic precursor of acetylcholine.[2] 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).[4]

Production

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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.[5][6]

Safety

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Alpha-GPC metabolizes to trimethylamine n-oxide 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.[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. PMID 12637119.
  2. ^ a b Parnetti 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. PMID 17331541. S2CID 34661218.
  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. PMID 14519085. S2CID 46175609.
  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 from the 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. PMID 24156263.
  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. PMID 23387341.
  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. PMC 8613599. PMID 34817582.
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