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Details

Stereochemistry RACEMIC
Molecular Formula 2C12H16N2O.C4H4O4
Molecular Weight 524.6086
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NEBRACETAM FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.NCC1CN(CC2=CC=CC=C2)C(=O)C1.NCC3CN(CC4=CC=CC=C4)C(=O)C3

InChI

InChIKey=LJHCLGIFHRYJFN-WXXKFALUSA-N
InChI=1S/2C12H16N2O.C4H4O4/c2*13-7-11-6-12(15)14(9-11)8-10-4-2-1-3-5-10;5-3(6)1-2-4(7)8/h2*1-5,11H,6-9,13H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+

HIDE SMILES / InChI

Molecular Formula C12H16N2O
Molecular Weight 204.2682
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Nebracetam (WEB1881FU) is a pyrrolidinone nootropic. Like other racetams, it is an aminomethyl pyrrolidinone derivative of piracetam. It was first synthesized in Germany in the late 1980s, where it was manufactured by Boehringer Ingelheim. Nebracetam is a M1-muscarinic agonist. In Jurkat cells Nebracetam induced a rise of [Ca2+]i in the medium with 1 mM Ca2+ and without Ca2+ (plus 1 mM EGTA). The nebracetam-induced [Ca2+]i rise was blocked by atropine greater than pirenzepine greater than AF-DX 116. Nebracetam facilitates the ganglionic muscarinic transmission through acting on presynaptic sites. Nebracetam has been investigated as a cognition-enhancing drug, but most of the studies have taken place in animal models. It has been shown to protect neurons in animals exposed to low levels of oxygen and low blood sugar. Nebracetam is also protective against glutamate toxicity, presumably via its modulation of calcium entry. In animal models of Alzheimer’s disease, nebracetam improved memory in a dose-dependent manner. It also protected against ischemia- (lack of oxygen) induced neuronal death in a rat model of stroke. The compound has also been tested as a possible antidepressant, presumably because its mechanism of action (reducing dopaminergic and serotonergic uptake) is similar to other commonly used antidepressants. Some studies have taken place in humans. A single dose was shown to alter brain waves in healthy volunteers, who showed increased alpha activity and an associated decrease of slow activity and of fast activity in the frontal cortex. These results imply that nebracetam might improve linguistic learning and memory processing. A trial in dementia patients reported that significant clinical improvement occurred after 8 weeks. However, other studies did not replicate this finding.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antidepressant activities of WEB 1881, a new nootropic agent.
1989 Sep-Oct
The importance of basic science and clinical research as a selection criterion for general surgery residency programs.
2008 Mar-Apr
Patents

Sample Use Guides

Dementia of the Alzheimer type: 800 mg/day (400 mg twice a day) for 8 weeks
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Nebracetam (10-100 uM) dose-dependently inhibited increases in intracellular Ca2+ concentrations evoked by various stimuli in cultured rat cerebellar granule cells. The magnitude of the nebracetam (100 uM)-induced inhibition of L-glutamate- and N-methyl-D-aspartate-evoked Ca2+ responses was 1.5-fold and 1.7-fold greater, respectively, than the inhibition of the high K(+)-evoked response. https://www.ncbi.nlm.nih.gov/pubmed/7745850
Acetylcholine release from the isolated dog ganglia by preganglionic stimulation (5 Hz) was enhanced in the presence of nebracetam, 10(-7) to 10(-5) M. Uptake of choline in the isolated ganglia was not altered by nebracetam (10(-6) M) but was enhanced under the depleted conditions.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:05:46 GMT 2023
Edited
by admin
on Sat Dec 16 09:05:46 GMT 2023
Record UNII
3GPZ0A8OW9
Record Status Validated (UNII)
Record Version
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Name Type Language
NEBRACETAM FUMARATE
MI  
Common Name English
(±)-4-(AMINOMETHYL)-1-BENZYL-2-PYRROLIDINONE FUMARATE
Systematic Name English
NEBRACETAM FUMARATE [MI]
Common Name English
NEBRACETAM FUMARATE [JAN]
Common Name English
2-PYRROLIDINONE, 4-(AMINOMETHYL)-1-(PHENYLMETHYL)-, (2E)-2-BUTENEDIOATE (2:1)
Systematic Name English
WEB-1881FU
Code English
Code System Code Type Description
CAS
97205-35-1
Created by admin on Sat Dec 16 09:05:46 GMT 2023 , Edited by admin on Sat Dec 16 09:05:46 GMT 2023
PRIMARY
PUBCHEM
6444388
Created by admin on Sat Dec 16 09:05:46 GMT 2023 , Edited by admin on Sat Dec 16 09:05:46 GMT 2023
PRIMARY
MERCK INDEX
m839
Created by admin on Sat Dec 16 09:05:46 GMT 2023 , Edited by admin on Sat Dec 16 09:05:46 GMT 2023
PRIMARY Merck Index
FDA UNII
3GPZ0A8OW9
Created by admin on Sat Dec 16 09:05:46 GMT 2023 , Edited by admin on Sat Dec 16 09:05:46 GMT 2023
PRIMARY
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ACTIVE MOIETY