MCOPPB | CAS#1028969-49-4 | nociceptin receptor agonist

MedKoo Cat#: 510271 | Name: MCOPPB

Description:

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

MCOPPB is a drug which acts as a potent and selective agonist for the nociceptin receptor, with a pKi of 10.07 and much weaker activity at other opioid receptors. It has only moderate affinity for the mu opioid receptor, weak affinity for the kappa opioid receptor and negligible binding at the delta opioid receptor. In animal studies, MCOPPB produces potent anxiolytic effects, with no inhibition of memory or motor function, and only slight sedative side effects which do not appear until much higher doses than the effective anxiolytic dose range. (http://en.wikipedia.org/wiki/MCOPPB)

Chemical Structure

MCOPPB

CAS#1028969-49-4 (free base)

Theoretical Analysis

MedKoo Cat#: 510271

Name: MCOPPB

CAS#: 1028969-49-4 (free base)

Chemical Formula: C26H40N4

Exact Mass: 408.3253

Molecular Weight: 408.62

Elemental Analysis: C, 76.42; H, 9.87; N, 13.71

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Related CAS #

1108147-88-1(HCl) 1028969-49-4 (free base)

Synonym

MCOPPB

IUPAC/Chemical Name

(R)-1-(1-(1-methylcyclooctyl)piperidin-4-yl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole

InChi Key

CYYNMPPFEJPBJD-OAQYLSRUSA-N

InChi Code

InChI=1S/C26H40N4/c1-26(15-7-3-2-4-8-16-26)29-18-13-22(14-19-29)30-24-12-6-5-11-23(24)28-25(30)21-10-9-17-27-20-21/h5-6,11-12,21-22,27H,2-4,7-10,13-20H2,1H3/t21-/m1/s1

SMILES Code

CC1(N2CCC(N3C4=CC=CC=C4N=C3[C@H]5CNCCC5)CC2)CCCCCCC1

Appearance

white to off-white 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

MCOPPB is a drug which acts as a potent and selective agonist for the nociceptin receptor, with a pKi of 10.07 and much weaker activity at other opioid receptors.

In vitro activity:

MCOPPB has a high affinity for the human NOP receptor (pKi = 10.07 +/- 0.01) and selectivity for the NOP receptor over other members of the opioid receptor family: 12-, 270- and >1000-fold more selective for the NOP receptor than for the micro-, kappa-, and delta-receptor, respectively. Reference: J Pharmacol Sci. 2008 Mar;106(3):361-8. https://pubmed.ncbi.nlm.nih.gov/18319566/

In vivo activity:

MCOPPB reduced the senescence cell burden in peripheral tissues but not in the central nervous system. Mice and worms exposed to MCOPPB also exhibited locomotion and lipid storage changes. Mechanistically, MCOPPB treatment activated transcriptional networks involved in the immune responses to external stressors, implicating Toll-like receptors (TLRs). Reference: Geroscience. 2022 Feb;44(1):463-483. https://pubmed.ncbi.nlm.nih.gov/34820764/

Preparing Stock Solutions

The following data is based on the product molecular weight 408.62 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

Formulation protocol:

1. Raffaele M, Kovacovicova K, Biagini T, Lo Re O, Frohlich J, Giallongo S, Nhan JD, Giannone AG, Cabibi D, Ivanov M, Tonchev AB, Mistrik M, Lacey M, Dzubak P, Gurska S, Hajduch M, Bartek J, Mazza T, Micale V, Curran SP, Vinciguerra M. Nociceptin/orphanin FQ opioid receptor (NOP) selective ligand MCOPPB links anxiolytic and senolytic effects. Geroscience. 2022 Feb;44(1):463-483. doi: 10.1007/s11357-021-00487-y. Epub 2021 Nov 24. PMID: 34820764; PMCID: PMC8612119. 2. Hirao A, Imai A, Sugie Y, Yamada Y, Hayashi S, Toide K. Pharmacological characterization of the newly synthesized nociceptin/orphanin FQ-receptor agonist 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole as an anxiolytic agent. J Pharmacol Sci. 2008 Mar;106(3):361-8. doi: 10.1254/jphs.fp0071742. Epub 2008 Mar 5. PMID: 18319566. 3. Hayashi S, Hirao A, Imai A, Nakamura H, Murata Y, Ohashi K, Nakata E. Novel non-peptide nociceptin/orphanin FQ receptor agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: design, synthesis, and structure-activity relationship of oral receptor occupancy in the brain for orally potent antianxiety drug. J Med Chem. 2009 Feb 12;52(3):610-25. doi: 10.1021/jm7012979. PMID: 19125610.

In vitro protocol:

In vivo protocol:

1. Raffaele M, Kovacovicova K, Biagini T, Lo Re O, Frohlich J, Giallongo S, Nhan JD, Giannone AG, Cabibi D, Ivanov M, Tonchev AB, Mistrik M, Lacey M, Dzubak P, Gurska S, Hajduch M, Bartek J, Mazza T, Micale V, Curran SP, Vinciguerra M. Nociceptin/orphanin FQ opioid receptor (NOP) selective ligand MCOPPB links anxiolytic and senolytic effects. Geroscience. 2022 Feb;44(1):463-483. doi: 10.1007/s11357-021-00487-y. Epub 2021 Nov 24. PMID: 34820764; PMCID: PMC8612119. 2. Hayashi S, Hirao A, Imai A, Nakamura H, Murata Y, Ohashi K, Nakata E. Novel non-peptide nociceptin/orphanin FQ receptor agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: design, synthesis, and structure-activity relationship of oral receptor occupancy in the brain for orally potent antianxiety drug. J Med Chem. 2009 Feb 12;52(3):610-25. doi: 10.1021/jm7012979. PMID: 19125610.

1: Hayashi S, Hirao A, Imai A, Nakamura H, Murata Y, Ohashi K, Nakata E. Novel non-peptide nociceptin/orphanin FQ receptor agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: design, synthesis, and structure-activity relationship of oral receptor occupancy in the brain for orally potent antianxiety drug. J Med Chem. 2009 Feb 12;52(3):610-25. doi: 10.1021/jm7012979. PubMed PMID: 19125610. 2: Hirao A, Imai A, Sugie Y, Yamada Y, Hayashi S, Toide K. Pharmacological characterization of the newly synthesized nociceptin/orphanin FQ-receptor agonist 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole as an anxiolytic agent. J Pharmacol Sci. 2008 Mar;106(3):361-8. Epub 2008 Mar 5. PubMed PMID: 18319566.