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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H20NO6P
Molecular Weight 257.2213
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHOLINE ALFOSCERATE

SMILES

C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO

InChI

InChIKey=SUHOQUVVVLNYQR-MRVPVSSYSA-N
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

HIDE SMILES / InChI
Choline alfoscerate (alpha-Glycerylphosphorylcholine or Alpha-GPC) is a nootropic choline-containing phospholipid. Choline alphoscerate increases the release of acetylcholine in rat hippocampus, facilitates learning and memory in experimental animals, improves brain transduction mechanisms and decreases age-dependent structural changes occurring in rat brain areas involved in learning and memory. The compound exerts neuroprotective effects in models of altered cholinergic neurotransmission and of brain vascular injury. In clinical studies choline alphoscerate improved memory and attention impairment, as well as affective and somatic symptoms in dementia disorders. In Europe alpha-GPC is a prescription medication for the treatment of Alzheimer's disease. It is available in two forms; one is taken by mouth, and the other is given as a shot. In the United States alpha-GPC is only available as a dietary supplement, mostly in products promoted to improve memory. Other uses for alpha-GPC include treatment of various kinds of dementia, stroke, and "mini-stroke" (transient ischemic attack, TIA). Alpha-GPC is also used for improving memory, thinking skills, and learning.

Originator

Curator's Comment: Schmidt et al., 1945 (Isolation); Aloisi, Buffa, 1948 and Baer, Kates, 1948 (Synthesis)

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Gliatilin

Approved Use

Unknown
Primary
Gliatilin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of a new cognition enhancer, alpha-glycerylphosphorylcholine, on scopolamine-induced amnesia and brain acetylcholine.
1991 Aug
Effect of L-alpha-glyceryl-phosphorylcholine on amnesia caused by scopolamine.
1991 Mar
Molecular mechanisms mediating the effects of L-alpha-glycerylphosphorylcholine, a new cognition-enhancing drug, on behavioral and biochemical parameters in young and aged rats.
1992 Sep
Patents

Sample Use Guides

In Vitro Use Guide
Unknown
Name Type Language
CHOLINE ALFOSCERATE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
CHOLINE ALFOSCERATE [MART.]
Common Name English
CHOLINE ALFOSCERATE [MI]
Common Name English
GLYCEROPHOSPHOCHOLINE
INCI  
INCI  
Official Name English
GLYCEROPHOSPHOCHOLINE [INCI]
Common Name English
choline alfoscerate [INN]
Common Name English
CHOLINE HYDROXIDE, (R)-2,3-DIHYDROXYPROPYL HYDROGEN PHOSPHATE, INNER SALT
Common Name English
L-ALPHA-GLYCERYLPHOSPHORYLCHOLINE [USP-RS]
Common Name English
L-.ALPHA.-GLYCERYLPHOSPHORYLCHOLINE
Brand Name English
Choline alfoscerate [WHO-DD]
Common Name English
ALPHA-GLYCERYLPHOSPHORYLCHOLINE
Common Name English
ETHANAMINIUM, 2-((((2R)-2,3-DIHYDROXYPROPOXXY)HYDROXYPHOSPHINYL)OXY)-N,N,N-TRIMETHYL-, INNER SALT
Common Name English
CHOLINE ALPHOSCERATE
Common Name English
GLIATILIN
Brand Name English
Classification Tree Code System Code
WHO-ATC N07AX02
Created by admin on Fri Dec 15 16:17:13 GMT 2023 , Edited by admin on Fri Dec 15 16:17:13 GMT 2023
LOINC 10578-3
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WHO-VATC QN07AX02
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DSLD 315 (Number of products:313)
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Code System Code Type Description
ECHA (EC/EINECS)
248-962-2
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DRUG BANK
DB04660
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WIKIPEDIA
Alpha-GPC
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GRAS Notification (GRN No.)
419
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EVMPD
SUB06216MIG
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CAS
28319-77-9
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RXCUI
4918
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SMS_ID
100000090092
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MERCK INDEX
m3482
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PRIMARY Merck Index
FDA UNII
60M22SGW66
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CHEBI
16870
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RS_ITEM_NUM
1295786
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EPA CompTox
DTXSID70951010
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INN
5203
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PUBCHEM
657272
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DRUG CENTRAL
627
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ChEMBL
CHEMBL1567463
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NCI_THESAURUS
C166883
Created by admin on Fri Dec 15 16:17:13 GMT 2023 , Edited by admin on Fri Dec 15 16:17:13 GMT 2023
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