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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
Structure of TERT-BUTYL PEROXYBENZOATE

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

HIDE SMILES / InChI

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

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

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
First isolation of monomeric N-alkoxyarylaminyl radicals and their chemical and magnetic properties.
2001 Nov 2
N-tert-Butoxy-1-aminopyrenyl Radicals. Isolation, Electronic Structure, and Magnetic Characterization.
2002 Dec 13
Determination of organic peroxides by liquid chromatography with on-line post-column ultraviolet irradiation and peroxyoxalate chemiluminescence detection.
2003 Feb 14
Unusual atmospheric pressure chemical ionization conditions for detection of organic peroxides.
2003 Sep
Asymmetric allylic oxidation reactions catalyzed by a chiral nonracemic and C2-symmetric 2,2'-bipyridyl copper(I) complex.
2006 Jan 7
Theoretical insights into enantioselective catalysis: the mechanism of the Kharasch-Sosnovsky reaction.
2008
Chiral boron-bridged bisoxazoline (borabox) ligands: structures and reactivities of Pd and Cu complexes.
2008
Synthesis and properties of a highly soluble dihydoxo(tetra-tert-butylphthalocyaninato)antimony(V) complex as a precursor toward water-soluble phthalocyanines.
2008 Mar
Novel selective allosteric activator of the M1 muscarinic acetylcholine receptor regulates amyloid processing and produces antipsychotic-like activity in rats.
2008 Oct 8
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 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
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 Fri Dec 15 15:08:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:34 GMT 2023
Record UNII
54E39145KT
Record Status Validated (UNII)
Record Version
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Name Type Language
TERT-BUTYL PEROXYBENZOATE
Systematic Name English
PEROXYBENZOIC ACID, T-BUTYL ESTER [HSDB]
Common Name English
BUTYL PEROXYBENZOATE, TERT-
Systematic Name English
TBPB
Common Name English
NSC-674
Code English
T-BUTYL BENZOYL PEROXIDE
INCI  
INCI  
Official Name English
TERT-BUTYL PERBENZOATE
Systematic Name English
T-BUTYL PEROXYBENZOATE
Systematic Name English
T-BUTYL BENZOYL PEROXIDE [INCI]
Common Name English
Code System Code Type Description
FDA UNII
54E39145KT
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
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PUBCHEM
11966
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
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WIKIPEDIA
tert-Butyl peroxybenzoate
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
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MESH
C060534
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
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CAS
614-45-9
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
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HSDB
2891
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
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EPA CompTox
DTXSID9024699
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
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ECHA (EC/EINECS)
210-382-2
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
PRIMARY
NSC
674
Created by admin on Fri Dec 15 15:08:34 GMT 2023 , Edited by admin on Fri Dec 15 15:08:34 GMT 2023
PRIMARY