Glycerophosphorylcholine

Chemical compound From Wikipedia, the free encyclopedia

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]

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Glycerophosphorylcholine
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Clinical data
ATC code
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Identifiers
  • [(2R)-2,3-Dihydroxypropyl] 2-trimethylazaniumylethyl phosphate
CAS Number
PubChem CID
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UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
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 Y
  • Key:SUHOQUVVVLNYQR-MRVPVSSYSA-N Y
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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

A retrospective cohort study involving 12 million participants in South Korea found that α-GPC users had a higher risk of stroke ( + 46 % ). The authors suggested that one possible explanation is that dysbiosis may lead to α-GPC being metabolized into trimethylamine (TMA) in the gastrointestinal tract, and then to trimethylamine N-oxide (TMAO) in the liver, which has implications for cardiovascular health. However, they also noted that the study could be influenced by confounding variables, as α-GPC is often prescribed to individuals with preexisting health risks.[7]

A later systematic review and meta-analysis criticized the statistical analysis of the South Korean cohort study, describing it as questionable and imprecise. The review concluded that α-GPC has a favorable safety and tolerability profile and is effective in improving cognitive function and daily living in patients with dementia disorders of neurological origin, adult-onset vascular dementia, and Alzheimer’s disease.[8]

References

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