TBPB

Modify Date: 2025-08-21 09:56:03

TBPB Structure
TBPB structure
Common Name TBPB
CAS Number 634616-95-8 Molecular Weight 404.548
Density 1.2±0.1 g/cm3 Boiling Point N/A
Molecular Formula C25H32N4O Melting Point N/A
MSDS USA Flash Point N/A

 Use of TBPB


TBPB is an allosteric M1 mAChR agonist(EC50=289 nM) that regulates amyloid processing and produces antipsychotic-like activity in rats.IC50 value: 289 nM(EC50) [2]Target: M1 mAChR agonistin vitro: TBPB activates M(1) through an allosteric site rather than the orthosteric acetylcholine binding site, which is likely critical for its unprecedented selectivity. Whole-cell patch-clamp recordings demonstrated that activation of M(1) by TBPB potentiates NMDA receptor currents in hippocampal pyramidal cells but does not alter excitatory or inhibitory synaptic transmission, responses thought to be mediated by M(2) and M(4) [1]. in vivo: TBPB was efficacious in models predictive of antipsychotic-like activity in rats at doses that did not produce catalepsy or peripheral adverse effects of other mAChR agonists [1].

 Names

Name 1-[1'-(2-Methylbenzyl)-1,4'-bipiperidin-4-yl]-1,3-dihydro-2H-benz imidazol-2-one
Synonym More Synonyms

 TBPB Biological Activity

Description TBPB is an allosteric M1 mAChR agonist(EC50=289 nM) that regulates amyloid processing and produces antipsychotic-like activity in rats.IC50 value: 289 nM(EC50) [2]Target: M1 mAChR agonistin vitro: TBPB activates M(1) through an allosteric site rather than the orthosteric acetylcholine binding site, which is likely critical for its unprecedented selectivity. Whole-cell patch-clamp recordings demonstrated that activation of M(1) by TBPB potentiates NMDA receptor currents in hippocampal pyramidal cells but does not alter excitatory or inhibitory synaptic transmission, responses thought to be mediated by M(2) and M(4) [1]. in vivo: TBPB was efficacious in models predictive of antipsychotic-like activity in rats at doses that did not produce catalepsy or peripheral adverse effects of other mAChR agonists [1].
Related Catalog
References

[1]. Jones CK, et al. Novel selective allosteric activator of the M1 muscarinic acetylcholine receptor regulates amyloid processing and produces antipsychotic-like activity in rats. J Neurosci. 2008 Oct 8;28(41):10422-33.

[2]. Miller NR, et al. Synthesis and SAR of analogs of the M1 allosteric agonist TBPB. Part II: Amides, sulfonamides and ureas--the effect of capping the distal basic piperidine nitrogen. Bioorg Med Chem Lett. 2008 Oct 15;18(20):5443-7.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Molecular Formula C25H32N4O
Molecular Weight 404.548
Exact Mass 404.257599
PSA 44.53000
LogP 4.96
Index of Refraction 1.623
InChIKey CWPKTBMRVATCBL-UHFFFAOYSA-N
SMILES Cc1ccccc1CN1CCC(N2CCC(n3c(=O)[nH]c4ccccc43)CC2)CC1
Storage condition 2-8℃

 Safety Information

RIDADR NONH for all modes of transport

 Synthetic Route

~75%

TBPB Structure

TBPB

CAS#:634616-95-8

Literature: Rasheed, Mohammed Abdul; Shaik, Nagul Meera; Nirogi, Ramakrishna Synthetic Communications, 2013 , vol. 43, # 13 p. 1796 - 1801

~82%

TBPB Structure

TBPB

CAS#:634616-95-8

Literature: Bridges, Thomas M.; Brady, Ashley E.; Phillip Kennedy; Nathan Daniels; Miller, Nicole R.; Kim, Kwango; Breininger, Micah L.; Gentry, Patrick R.; Brogan, John T.; Jones, Carrie K.; Jeffrey Conn; Lindsley, Craig W. Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 20 p. 5439 - 5442

~%

TBPB Structure

TBPB

CAS#:634616-95-8

Literature: Rasheed, Mohammed Abdul; Shaik, Nagul Meera; Nirogi, Ramakrishna Synthetic Communications, 2013 , vol. 43, # 13 p. 1796 - 1801

~%

TBPB Structure

TBPB

CAS#:634616-95-8

Literature: Rasheed, Mohammed Abdul; Shaik, Nagul Meera; Nirogi, Ramakrishna Synthetic Communications, 2013 , vol. 43, # 13 p. 1796 - 1801

~%

TBPB Structure

TBPB

CAS#:634616-95-8

Literature: Rasheed, Mohammed Abdul; Shaik, Nagul Meera; Nirogi, Ramakrishna Synthetic Communications, 2013 , vol. 43, # 13 p. 1796 - 1801

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 TBPBBioassay

View more

Name: Agonist activity at muscarinic M3 receptor
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M3
External Id: CHEMBL983584
Name: Displacement of [3H]NMS from rat muscarinic M1 receptor expressed in CHO cells after ...
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M1
External Id: CHEMBL2319076
Name: Agonist activity at muscarinic M2 receptor
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M2
External Id: CHEMBL983583
Name: Agonist activity at muscarinic M5 receptor
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M5
External Id: CHEMBL983586
Name: Agonist activity at muscarinic M4 receptor
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M4
External Id: CHEMBL983585
Name: Agonist activity at muscarinic M1 receptor relative to carbachol
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M1
External Id: CHEMBL983580
Name: Agonist activity at muscarinic M1 receptor
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M1
External Id: CHEMBL983579
Name: Inhibition of dopamine D2 receptor
Source: ChEMBL
Target: D(2) dopamine receptor
External Id: CHEMBL983581
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 Synonyms

2-Pyrrolo-1,3,2-dioxa-phospholan
1-[1'-(2-Methylbenzyl)-1,4'-bipiperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
2-pyrrol-1-yl-1,3,2-dioxaphospholan
TBPB
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