TBPB | CAS#634616-95-8 | Muscarinic M1 Receptor Allosteric Agonist

MedKoo Cat#: 522531 | Name: TBPB

Description:

WARNING: This product is for research use only, not for human or veterinary use.

TBPB is a highly selective Muscarinic M1 receptor allosteric agonist. TBPB activates M1 through an allosteric site rather than the orthosteric acetylcholine binding site, which is likely critical for its selectivity. TBPB displays unprecedented functional selectivity at the M₁ mAChR. TBPB is a bitopic ligand, interacting with both the orthosteric site and an allosteric site, at the M₁ mAChR.

Chemical Structure

TBPB

CAS#634616-95-8

Theoretical Analysis

MedKoo Cat#: 522531

Name: TBPB

CAS#: 634616-95-8

Chemical Formula: C25H32N4O

Exact Mass: 404.2576

Molecular Weight: 404.56

Elemental Analysis: C, 74.22; H, 7.97; N, 13.85; O, 3.95

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to ship
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 850.00	Ready to ship
500mg	USD 1,250.00	Ready to ship
1g	USD 1,850.00	Ready to ship
2g	USD 2,950.00	2 weeks

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Related CAS #

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Synonym

TBPB

IUPAC/Chemical Name

1-(1′-(2-Methylbenzyl)-1,4′-bipiperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

InChi Key

CWPKTBMRVATCBL-UHFFFAOYSA-N

InChi Code

InChI=1S/C25H32N4O/c1-19-6-2-3-7-20(19)18-27-14-10-21(11-15-27)28-16-12-22(13-17-28)29-24-9-5-4-8-23(24)26-25(29)30/h2-9,21-22H,10-18H2,1H3,(H,26,30)

SMILES Code

O=C1N(C2CCN(C3CCN(CC4=CC=CC=C4C)CC3)CC2)C5=CC=CC=C5N1

Appearance

White to beige solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#X7P07R31

QC Data

View QC data: current batch, Lot#X7P07R31

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 404.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Zivkovic AR, Sedlaczek O, von Haken R, Schmidt K, Brenner T, Weigand MA, Bading H, Bengtson CP, Hofer S. Muscarinic M1 receptors modulate endotoxemia-induced loss of synaptic plasticity. Acta Neuropathol Commun. 2015 Nov 4;3:67. doi: 10.1186/s40478-015-0245-8. PubMed PMID: 26531194; PubMed Central PMCID: PMC4632469. 2: Chen X, Klöckner J, Holze J, Zimmermann C, Seemann WK, Schrage R, Bock A, Mohr K, Tränkle C, Holzgrabe U, Decker M. Rational design of partial agonists for the muscarinic m1 acetylcholine receptor. J Med Chem. 2015 Jan 22;58(2):560-76. doi: 10.1021/jm500860w. Epub 2014 Dec 19. PubMed PMID: 25478907. 3: Keov P, López L, Devine SM, Valant C, Lane JR, Scammells PJ, Sexton PM, Christopoulos A. Molecular mechanisms of bitopic ligand engagement with the M1 muscarinic acetylcholine receptor. J Biol Chem. 2014 Aug 22;289(34):23817-37. doi: 10.1074/jbc.M114.582874. Epub 2014 Jul 8. PubMed PMID: 25006252; PubMed Central PMCID: PMC4156061. 4: Keov P, Valant C, Devine SM, Lane JR, Scammells PJ, Sexton PM, Christopoulos A. Reverse engineering of the selective agonist TBPB unveils both orthosteric and allosteric modes of action at the M₁ muscarinic acetylcholine receptor. Mol Pharmacol. 2013 Sep;84(3):425-37. doi: 10.1124/mol.113.087320. Epub 2013 Jun 24. PubMed PMID: 23798605. 5: Sheffler DJ, Sevel C, Le U, Lovell KM, Tarr JC, Carrington SJ, Cho HP, Digby GJ, Niswender CM, Conn PJ, Hopkins CR, Wood MR, Lindsley CW. Further exploration of M₁ allosteric agonists: subtle structural changes abolish M₁ allosteric agonism and result in pan-mAChR orthosteric antagonism. Bioorg Med Chem Lett. 2013 Jan 1;23(1):223-7. doi: 10.1016/j.bmcl.2012.10.132. Epub 2012 Nov 9. PubMed PMID: 23200253; PubMed Central PMCID: PMC3525729. 6: Jacobson MA, Kreatsoulas C, Pascarella DM, O'Brien JA, Sur C. 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. Mol Pharmacol. 2010 Oct;78(4):648-57. doi: 10.1124/mol.110.065771. Epub 2010 Jul 21. PubMed PMID: 20660086. 7: Thomsen M, Conn PJ, Lindsley C, Wess J, Boon JY, Fulton BS, Fink-Jensen A, Caine SB. Attenuation of cocaine's reinforcing and discriminative stimulus effects via muscarinic M1 acetylcholine receptor stimulation. J Pharmacol Exp Ther. 2010 Mar;332(3):959-69. doi: 10.1124/jpet.109.162057. Epub 2009 Dec 8. PubMed PMID: 19996296; PubMed Central PMCID: PMC2835434. 8: Jones CK, Brady AE, Davis AA, Xiang Z, Bubser M, Tantawy MN, Kane AS, Bridges TM, Kennedy JP, Bradley SR, Peterson TE, Ansari MS, Baldwin RM, Kessler RM, Deutch AY, Lah JJ, Levey AI, Lindsley CW, Conn PJ. 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. doi: 10.1523/JNEUROSCI.1850-08.2008. PubMed PMID: 18842902; PubMed Central PMCID: PMC2577155. 9: Miller NR, Daniels RN, Bridges TM, Brady AE, Conn PJ, Lindsley CW. 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. doi: 10.1016/j.bmcl.2008.09.032. Epub 2008 Sep 11. PubMed PMID: 18829311; PubMed Central PMCID: PMC3177607. 10: Bridges TM, Brady AE, Kennedy JP, Daniels RN, Miller NR, Kim K, Breininger ML, Gentry PR, Brogan JT, Jones CK, Conn PJ, Lindsley CW. Synthesis and SAR of analogues of the M1 allosteric agonist TBPB. Part I: Exploration of alternative benzyl and privileged structure moieties. Bioorg Med Chem Lett. 2008 Oct 15;18(20):5439-42. doi: 10.1016/j.bmcl.2008.09.023. Epub 2008 Sep 10. PubMed PMID: 18805692; PubMed Central PMCID: PMC3177598.