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
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 |
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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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Detection of volatile organic peroxides in indoor air. | 2001 Dec |
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First isolation of monomeric N-alkoxyarylaminyl radicals and their chemical and magnetic properties. | 2001 Nov 2 |
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N-tert-Butoxy-1-aminopyrenyl Radicals. Isolation, Electronic Structure, and Magnetic Characterization. | 2002 Dec 13 |
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Isolation and magnetic properties of heterocycle-carrying N-alkoxyarylaminyl radicals. | 2003 Dec 26 |
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Determination of organic peroxides by liquid chromatography with on-line post-column ultraviolet irradiation and peroxyoxalate chemiluminescence detection. | 2003 Feb 14 |
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Unusual atmospheric pressure chemical ionization conditions for detection of organic peroxides. | 2003 Sep |
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Exposure of mouse skin to organic peroxides: subchronic effects related to carcinogenic potential. | 2004 Mar |
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Asymmetric allylic oxidation reactions catalyzed by a chiral nonracemic and C2-symmetric 2,2'-bipyridyl copper(I) complex. | 2006 Jan 7 |
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Theoretical insights into enantioselective catalysis: the mechanism of the Kharasch-Sosnovsky reaction. | 2008 |
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Chiral boron-bridged bisoxazoline (borabox) ligands: structures and reactivities of Pd and Cu complexes. | 2008 |
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Synthesis and properties of a highly soluble dihydoxo(tetra-tert-butylphthalocyaninato)antimony(V) complex as a precursor toward water-soluble phthalocyanines. | 2008 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.
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54E39145KT
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11966
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tert-Butyl peroxybenzoate
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C060534
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614-45-9
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DTXSID9024699
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210-382-2
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674
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SUBSTANCE RECORD