Chemistry:Glycerophosphorylcholine

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Short description: Chemical compound
Glycerophosphorylcholine
L-alpha-GPC Structural Formula V.1.svg
Clinical data
ATC code
Legal status
Legal status
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CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
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Chemical and physical data
FormulaC8H20NO6P
Molar mass257.223 g·mol−1
3D model (JSmol)
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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

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

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

  1. "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. January 2003. doi:10.1016/S0149-2918(03)90023-3. PMID 12637119. 
  2. 2.0 2.1 "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. June 2007. doi:10.1016/j.jns.2007.01.043. PMID 17331541. 
  3. "Treatment of dementia with neurotransmission modulation". Expert Opinion on Investigational Drugs 12 (10): 1633–54. October 2003. doi:10.1517/13543784.12.10.1633. PMID 14519085. 
  4. "Generally Recognized as Safe (GRAS) Determination for the Use of AlphaSize® Alpha-Glycerylphosphoryl Choline". United States Food and Drug Administration. 25 January 2012. https://www.accessdata.fda.gov/scripts/fcn/gras_notices/GRN000419.pdf. 
  5. E. Traini, V. Bramanti, F. Amenta (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): 1070–1079, doi:10.2174/15672050113106660173, PMID 24156263 
  6. P. L. Scapicchio (2013), "Revisiting choline alphoscerate profile: a new, perspective, role in dementia?", The International Journal of Neuroscience 123 (7): 444–449, doi:10.3109/00207454.2013.765870, PMID 23387341 
  7. Lee, G; Choi, S; Chang, J; Choi, D; Son, JS; Kim, K; Kim, SM; Jeong, S et al. (1 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. PMID 34817582. 

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