Glycerophosphorylcholine

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]

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
ECHA InfoCard100.044.496
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)

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]

References
  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. 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. 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, vol. 10, no. 10, pp. 1070–1079, PMID 24156263{{citation}}: CS1 maint: multiple names: authors list (link)
  6. P. L. Scapicchio (2013), "Revisiting choline alphoscerate profile: a new, perspective, role in dementia?", The International Journal of Neuroscience, vol. 123, no. 7, pp. 444–449, doi:10.3109/00207454.2013.765870, PMID 23387341
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