Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H14O3 |
Molecular Weight | 194.2271 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)OOC(=O)C1=CC=CC=C1
InChI
InChIKey=GJBRNHKUVLOCEB-UHFFFAOYSA-N
InChI=1S/C11H14O3/c1-11(2,3)14-13-10(12)9-7-5-4-6-8-9/h4-8H,1-3H3
Molecular Formula | C11H14O3 |
Molecular Weight | 194.2271 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18842902
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18842902
TBPB was developed as a highly selective Muscarinic M1 receptor allosteric agonist. It activates M1 through an allosteric site rather than the orthosteric acetylcholine binding site, which is likely critical for its selectivity. The selective activation of M1 may provide a novel therapeutic approach for the treatment of psychotic symptoms associated with schizophrenia and Alzheimer’s disease.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18842902
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18842902 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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First isolation of monomeric N-alkoxyarylaminyl radicals and their chemical and magnetic properties. | 2001 Nov 2 |
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Isolation and magnetic properties of heterocycle-carrying N-alkoxyarylaminyl radicals. | 2003 Dec 26 |
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Exposure of mouse skin to organic peroxides: subchronic effects related to carcinogenic potential. | 2004 Mar |
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Novel selective allosteric activator of the M1 muscarinic acetylcholine receptor regulates amyloid processing and produces antipsychotic-like activity in rats. | 2008 Oct 8 |
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The M1 muscarinic receptor allosteric agonists AC-42 and 1-[1'-(2-methylbenzyl)-1,4'-bipiperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one bind to a unique site distinct from the acetylcholine orthosteric site. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18842902
in rats: the effects of TBPB (30, 56.6 and 100 mg/kg sc) on locomotor activity when administered alone were assessed in nonhabituated naive rats. In this experiment, rats were pretreated with veh or dose of TBPB for 30 minutes, then placed into the open field chambers and changes in locomotor activity were assessed for 60 min.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18842902
TBPB increases non-amyloidogenic amyloid precursor protein (APP) processing. In the study, PC12 cells over-expressing human sequence APP and M1 were treated with vehicle or TBPB, and the conditioned media were analyzed for APP derivatives. Treatment with 1 μM TBPB increased the shedding of APPsα, the ectodomain released by α-secretase cleavage, by 58% as compared to vehicle-treated cells. In TBPB treated cells, Aβ40 levels were reduced to 61% of the vehicle control and this effect was blocked by atropine. Together, these results are consistent with the hypothesis that selective activation of M1 could regulate APP processing and indicate that activation of M1 with TBPB shifts the processing of APP toward the non-amyloidogenic pathway, resulting in increased shedding of APPsα and decreased production of Aβ.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:08:34 GMT 2023
by
admin
on
Fri Dec 15 15:08:34 GMT 2023
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Record UNII |
54E39145KT
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Record Status |
Validated (UNII)
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Record Version |
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