Choline alfoscerate

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Choline alfoscerate
Clinical data
ATC code	N07AX02 (WHO) ;
Legal status
Legal status	In general: Over-the-counter (OTC);
Identifiers
	IUPAC name [(2S)-2,3-Dihydroxypropyl] 2-trimethylazaniumylethyl phosphate;
CAS Number	28319-77-9 ;
PubChem CID	71920;
ChemSpider	571409 ;
ChEBI	CHEBI:55397 ;
ChEMBL	ChEMBL1567463 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C8H20NO6P
Molar mass	257.221 g/mol
3D model (JSmol)	Interactive image;
	SMILES [O-]P(=O)(OC[C@H](O)CO)OCC[N+](C)(C)C;
	InChI 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 ; Key:SUHOQUVVVLNYQR-MRVPVSSYSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

L-Alpha glycerylphosphorylcholine (alpha-GPC, choline alfoscerate) is a natural choline compound found in the brain. It is also a parasympathomimetic acetylcholine precursor^[1] which may have potential for the treatment of Alzheimer's disease^[2] and dementia.^[3]

Alpha-GPC rapidly delivers choline to the brain across the blood–brain barrier and is a biosynthetic precursor of the acetylcholine neurotransmitter.^[2] It is a non-prescription drug in most countries and in the United States it is classified as generally recognized as safe (GRAS).^[4]

Efficacy

Studies have investigated the efficacy of alpha-GPC for cognitive disorders including stroke and Alzheimer’s disease. An Italian multicentre clinical trial on 2,044 patients suffering from recent stroke were supplied alpha-GPC in doses of 1,000 mg/day for 28 days and 400 mg three times per day for the five ensuing months. The trial confirmed the therapeutic role of alpha-GPC on the cognitive recovery of patients based on four measurement scales, three of which reached statistical significance.^[5] Commonly used doses are 300 to 1,200 mg daily.^[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.^{[citation needed]}

Storage

Many users report degradation of alpha-GPC when stored openly or for long periods of time. Alpha-GPC is hygroscopic and will pull moisture in from the surrounding air. This will cause the powder to turn into what appears to be a gel. Alpha-GPC with >99% purity will undergo this process at a visible rate (seconds to minutes) and thus requires minimized exposure to the air. This hygroscopic quality can cause gel capsules not fully packed with alpha-GPC to dissolve. Proper storage methods need to be used with alpha-GPC and include removing all air from the container, double bagging with plastic bags rated for chemicals (less likely to leak air), and storing bulk/excess inside the freezer. Vacuum sealed bags are highly recommended. For people accessing alpha-GPC daily it is advisable to separate a month's supply from excess and storing the excess as best as possible. Vacuum sealing a large supply into many 1 month dividends is a method positively reported by many users. It is important to note that hygroscopy is not degradation and leaves the substance still usable, however, the ability to accurately weigh a dose is no longer possible as the substance being weighed will be a mixture of powder and water. Liquefied or gelled alpha-GPC may also be indicative of poor storage and thus have an increased likelihood of actual degradation.^{[citation needed]}

References

↑ 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". Clin Ther. 25 (1): 178–93. doi:10.1016/S0149-2918(03)90023-3. PMID 12637119.
↑ ^2.0 ^2.1 Parnetti, Lucilla; et al. (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.
↑ Doggrell SA & Evans S; Evans (October 2003). "Treatment of dementia with neurotransmission modulation". Expert Opin Investig Drugs. 12 (10): 1633–1654. doi:10.1517/13543784.12.10.1633. PMID 14519085.
↑ ^4.0 ^4.1 US Food and Drug Administration: Generally Recognized as Safe (GRAS) Determination for the Use of AlphaSize Alpha-Glycerylphosphoryl Choline
↑ Barbagallo Sangiorgi, G; Barbagallo, M; Giordano, M; Meli, M; Panzarasa, R (1994). "Alpha-Glycerophosphocholine in the mental recovery of cerebral ischemic attacks. An Italian multicenter clinical trial". Ann NY Acad Sci. 717: 253–69. PMID 8030842.

Template:Nootropics

[pmid12637119-1] 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". Clin Ther. 25 (1): 178–93. doi:10.1016/S0149-2918(03)90023-3. PMID 12637119.

[Parnetti-2] 2.0 ^2.1 Parnetti, Lucilla; et al. (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.

[Doggrell-3] Doggrell SA & Evans S; Evans (October 2003). "Treatment of dementia with neurotransmission modulation". Expert Opin Investig Drugs. 12 (10): 1633–1654. doi:10.1517/13543784.12.10.1633. PMID 14519085.

[FDA-4] 4.0 ^4.1 US Food and Drug Administration: Generally Recognized as Safe (GRAS) Determination for the Use of AlphaSize Alpha-Glycerylphosphoryl Choline

[5] Barbagallo Sangiorgi, G; Barbagallo, M; Giordano, M; Meli, M; Panzarasa, R (1994). "Alpha-Glycerophosphocholine in the mental recovery of cerebral ischemic attacks. An Italian multicenter clinical trial". Ann NY Acad Sci. 717: 253–69. PMID 8030842.

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Clinical data

ATC code	N07AX02 (WHO)
Legal status
Legal status	In general: Over-the-counter (OTC)
Identifiers
IUPAC name [(2S)-2,3-Dihydroxypropyl] 2-trimethylazaniumylethyl phosphate
CAS Number	28319-77-9^N
PubChem CID	71920
ChemSpider	571409^Y
ChEBI	CHEBI:55397^Y
ChEMBL	ChEMBL1567463^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₈H₂₀NO₆P
Molar mass	257.221 g/mol
3D model (JSmol)	Interactive image
SMILES [O-]P(=O)(OC[C@H](O)CO)OCC[N+](C)(C)C
InChI 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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