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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

Molecular Formula C8H20NO6P
Molecular Weight 257.2213
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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 L-alpha-glyceryl-phosphorylcholine on amnesia caused by scopolamine.
1991 Mar
Correlation of antiphospholipid antibody recognition with the structure of synthetic oxidized phospholipids. Importance of Schiff base formation and aldol condensation.
2002 Mar 1
Patents

Sample Use Guides

In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:44:11 UTC 2023
Edited
by admin
on Wed Jul 05 23:44:11 UTC 2023
Record UNII
60M22SGW66
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
LOINC 10578-3
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
WHO-VATC QN07AX02
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
DSLD 315 (Number of products:313)
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
248-962-2
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
DRUG BANK
DB04660
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
WIKIPEDIA
Alpha-GPC
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
419
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
EVMPD
SUB06216MIG
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
CAS
28319-77-9
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
RXCUI
4918
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
SMS_ID
100000090092
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
MERCK INDEX
M3482
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY Merck Index
FDA UNII
60M22SGW66
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
CHEBI
16870
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
RS_ITEM_NUM
1295786
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID70951010
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
INN
5203
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
PUBCHEM
657272
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
DRUG CENTRAL
627
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL1567463
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
NCI_THESAURUS
C166883
Created by admin on Wed Jul 05 23:44:12 UTC 2023 , Edited by admin on Wed Jul 05 23:44:12 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY