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Glycerophosphorylcholine

From Wikipedia, the free encyclopedia
(Redirected fromGlycerophosphocholine)
Chemical compound

Pharmaceutical compound
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 mass257.223 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 naturalcholine compound found in the brain. It is also aparasympathomimeticacetylcholine precursor[1] which has been investigated for its potential for the treatment ofAlzheimer's disease[2] and otherdementias.[3]

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

Production

[edit]

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

Safety

[edit]

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

A latersystematic review andmeta-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 withdementia disorders of neurological origin, adult-onsetvascular dementia, andAlzheimer’s disease.[8]

References

[edit]
  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. ^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.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 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.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.ISSN 2574-3805.PMC 8613599.PMID 34817582.S2CID 244529061.
  8. ^Sagaro GG, Traini E, Amenta F (2023-03-07)."Activity of Choline Alphoscerate on Adult-Onset Cognitive Dysfunctions: A Systematic Review and Meta-Analysis".Journal of Alzheimer's Disease.92 (1):59–70.doi:10.3233/JAD-221189.PMC 10041421.PMID 36683513.S2CID 256104555.

External links

[edit]
Types
Vitamins and
chemical elements
("minerals")
Other common
ingredients
Related articles
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
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