Choline glycerophosphate

Names

[ Name ]:
Choline glycerophosphate

[Synonym ]:
L-α-Glycerophosphocholine
α-GPC
Ethanaminium, 2-[[[(2R)-2,3-dihydroxypropoxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-, inner salt
L-a-Glycerylphosphorylcholine
L-α-Glycerophosphorylcholine
Choline Alfoscerate
cholini alfosceras
(R)-2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium hydroxide inner salt
sn-Glycero-3-phosphocholine
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphate
MFCD00063544
alfoscerato de colina
EINECS 248-962-2
alfoscerate de choline
L-α Glycerylphosphorylcholine
L-a-GPC
sn-Glycero-3-phosphorylcholine
Choline glycerophosphate

Biological Activity

[Description]:

L-Alpha glycerylphosphorylcholine (alpha-GPC, choline alfoscerate) is a natural choline compound found in the brain and in milk. It is also a parasympathomimetic acetylcholine precursor which may have potential for the treatment of Alzheimer's disease and dementia.IC50 value:Target: Anti-ADAlpha-GPC rapidly delivers choline to the brain across the blood–brain barrier and is a biosynthetic precursor of the acetylcholine neurotransmitter. It is a non-prescription drug in most countries due to its Generally Recognised As Safe (GRAS) status [1]. Studies have investigated its efficacy 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 [2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> AChE

Natural Products >> Others

Research Areas >> Neurological Disease

[Target]

Human Endogenous Metabolite

[References]

[1]. Parnetti L, et al. Cholinergic precursors in the treatment of cognitive impairment of vascular origin: ineffective approaches or need for re-evaluation J Neurol Sci. 2007 Jun 15;257(1-2):264-9.

[2]. Barbagallo Sangiorgi G, et al. Alpha-Glycerophosphocholine in the mental recovery of cerebral ischemic attacks." An Italian multicenter clinical trial. Ann NY Acad Sci 1994; 717:253-69.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
-98ºC

[ Molecular Formula ]:
C₈H₂₀NO₆P

[ Molecular Weight ]:
257.221

[ Flash Point ]:
11 °C

[ Exact Mass ]:
257.102814

[ PSA ]:
108.86000

[ LogP ]:
-5.63

[ Appearance of Characters ]:
solid

[ Index of Refraction ]:
1.329 (20ºC)

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KH2775000

CHEMICAL NAME :: Ethanaminium, 2-(((2,3-dihydroxypropoxy)hydroxyphosphinyl)oxy)-N,N, N-trimethyl-, hydroxide, inner salt, (R)-

CAS REGISTRY NUMBER :: 28319-77-9

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C8-H20-N-O6-P

MOLECULAR WEIGHT :: 257.26

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >13 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #93-32553

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >650 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #93-32553

Safety Information

[ Hazard Codes ]:
F: Flammable;T: Toxic;

[ Risk Phrases ]:
R11

[ Safety Phrases ]:
S16-S36/37-S45

[ RIDADR ]:
UN 1230 3/PG 2

[ WGK Germany ]:
2

[ RTECS ]:
KH2775000

[ Packaging Group ]:
II

[ HS Code ]:
2923900090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2923900090

[ Summary ]:
2923900090 other quaternary ammonium salts and hydroxides。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%