BAN-ORL-24 HCl
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MedKoo CAT#: 530397

CAS#: 1401463-54-4 (HCl)

Description: BAN-ORL-24 is a Potent and selective NOP receptor antagonist. NOP receptor mediates anti-analgesia induced by agonist-antagonist opioids.

Chemical Structure

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BAN-ORL-24 HCl
CAS# 1401463-54-4 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 530397
Name: BAN-ORL-24 HCl
CAS#: 1401463-54-4 (HCl)
Chemical Formula: C27H37Cl2N3O2
Exact Mass: 0.00
Molecular Weight: 506.512
Elemental Analysis: C, 64.03; H, 7.36; Cl, 14.00; N, 8.30; O, 6.32

Price and Availability

Size Price Availability Quantity
5mg USD 350 3-4 months
10mg USD 550 3-4 months
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Related CAS #: 1401463-54-4 (HCl)   475150-69-7 (free base),  

Synonym: BAN-ORL-24 HCl; BAN-ORL-24 dihydrochloride; BAN-ORL24; BAN-ORL 24; BANORL-24; BANORL 24; BANORL24; BAN ORL 24.

IUPAC/Chemical Name: (2R)-1-Benzyl-N-(3-spiro[isobenzofuran-1(3H),4'-piperidin]-1'-ylpropyl)-2-pyrrolidinecarboxamide dihydrochloride.

InChi Key: NEEVITHVDIQNJY-KHZPMNTOSA-N

InChi Code: InChI=1S/C27H35N3O2.2ClH/c31-26(25-12-6-17-30(25)20-22-8-2-1-3-9-22)28-15-7-16-29-18-13-27(14-19-29)24-11-5-4-10-23(24)21-32-27;;/h1-5,8-11,25H,6-7,12-21H2,(H,28,31);2*1H/t25-;;/m1../s1

SMILES Code: O=C([C@@H]1N(CC2=CC=CC=C2)CCC1)NCCCN3CCC4(CC3)OCC5=C4C=CC=C5.[H]Cl.[H]Cl

Appearance: 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

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: Related CAS# 475150-69-7 (BAN-ORL-24 free base) 1401463-54-4 (BAN-ORL-24 dihydrochloride)

Product Data:
Product Data
Instruction:
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Biological target: BAN ORL 24 is a NOP receptor antagonist.
In vitro activity: In vitro studies were performed measuring receptor and [(35)S]GTPgammaS binding and calcium mobilization in cells expressing the recombinant NOP receptor as well as using N/OFQ sensitive tissues. BAN ORL 24 produced a concentration-dependent displacement of [(3)H]N/OFQ binding to CHO(hNOP) cell membranes showing high affinity (pK(i) 9.62) and selectivity (1000 fold) over classical opioid receptors. Furthermore, BAN ORL 24 antagonized with high potency the following in vitro effects of N/OFQ: stimulation of [(35)S]GTPgammaS binding in CHO(hNOP) cell membranes (pA(2) 9.98), calcium mobilization in CHO(hNOP) cells expressing the Galpha(qi5) chimeric protein (pK(B) 8.73), inhibition of electrically evoked twitches in the mouse (pA(2) 8.44) and rat (pK(B) 8.28) vas deferens, and in the guinea pig ileum (pK(B) 9.12). Reference: Eur J Pharmacol. 2009 Jul 1;614(1-3):50-7. https://www.sciencedirect.com/science/article/abs/pii/S0014299909004142?via%3Dihub
In vivo activity: In vivo, in the mouse tail withdrawal assay, BAN ORL 24 at 10 mg/kg antagonized the pronociceptive and antinociceptive effects of 1 nmol N/OFQ given supraspinally and spinally, respectively. Under the same experimental conditions BAN ORL 24 did not affect the antinociceptive action of 3 nmol endomorphin-1 injected intrathecally. Reference: Eur J Pharmacol. 2009 Jul 1;614(1-3):50-7. https://www.sciencedirect.com/science/article/abs/pii/S0014299909004142?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 200.0 394.86
Water 50.0 98.71

Preparing Stock Solutions

The following data is based on the product molecular weight 506.51 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.

Recalculate based on batch purity %
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. Fischetti C, Camarda V, Rizzi A, Pelà M, Trapella C, Guerrini R, McDonald J, Lambert DG, Salvadori S, Regoli D, Calo' G. Pharmacological characterization of the nociceptin/orphanin FQ receptor non peptide antagonist Compound 24. Eur J Pharmacol. 2009 Jul 1;614(1-3):50-7. doi: 10.1016/j.ejphar.2009.04.054. Epub 2009 May 12. PMID: 19445927.
In vitro protocol: 1. Fischetti C, Camarda V, Rizzi A, Pelà M, Trapella C, Guerrini R, McDonald J, Lambert DG, Salvadori S, Regoli D, Calo' G. Pharmacological characterization of the nociceptin/orphanin FQ receptor non peptide antagonist Compound 24. Eur J Pharmacol. 2009 Jul 1;614(1-3):50-7. doi: 10.1016/j.ejphar.2009.04.054. Epub 2009 May 12. PMID: 19445927.
In vivo protocol: 1. Fischetti C, Camarda V, Rizzi A, Pelà M, Trapella C, Guerrini R, McDonald J, Lambert DG, Salvadori S, Regoli D, Calo' G. Pharmacological characterization of the nociceptin/orphanin FQ receptor non peptide antagonist Compound 24. Eur J Pharmacol. 2009 Jul 1;614(1-3):50-7. doi: 10.1016/j.ejphar.2009.04.054. Epub 2009 May 12. PMID: 19445927.

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1: Awwad HO, Durand CD, Gonzalez LP, Tompkins P, Zhang Y, Lerner MR, Brackett DJ, Sherry DM, Awasthi V, Standifer KM. Post-blast treatment with Nociceptin/Orphanin FQ peptide (NOP) receptor antagonist reduces brain injury-induced hypoxia and signaling proteins in vestibulomotor-related brain regions. Behav Brain Res. 2016 Oct 25. pii: S0166-4328(16)30918-4. doi: 10.1016/j.bbr.2016.10.041. [Epub ahead of print] PubMed PMID: 27793733.

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6: Kallupi M, Oleata CS, Luu G, Teshima K, Ciccocioppo R, Roberto M. MT-7716, a novel selective nonpeptidergic NOP receptor agonist, effectively blocks ethanol-induced increase in GABAergic transmission in the rat central amygdala. Front Integr Neurosci. 2014 Feb 18;8:18. doi: 10.3389/fnint.2014.00018. PubMed PMID: 24600360; PubMed Central PMCID: PMC3927450.

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8: Rawls SM, Schroeder JA, Ding Z, Rodriguez T, Zaveri N. NOP receptor antagonist, JTC-801, blocks cannabinoid-evoked hypothermia in rats. Neuropeptides. 2007 Aug;41(4):239-47. PubMed PMID: 17512052.

9: Cerlesi MC, Ding H, Bird MF, Kiguchi N, Ferrari F, Malfacini D, Rizzi A, Ruzza C, Lambert DG, Ko MC, Calo G, Guerrini R. Pharmacological studies on the NOP and opioid receptor agonist PWT2-[Dmt(1)]N/OFQ(1-13). Eur J Pharmacol. 2017 Jan 5;794:115-126. doi: 10.1016/j.ejphar.2016.11.026. PubMed PMID: 27871910; PubMed Central PMCID: PMC5183561.

10: Pedregal C, Joshi EM, Toledo MA, Lafuente C, Diaz N, Martinez-Grau MA, Jiménez A, Benito A, Navarro A, Chen Z, Mudra DR, Kahl SD, Rash KS, Statnick MA, Barth VN. Development of LC-MS/MS-based receptor occupancy tracers and positron emission tomography radioligands for the nociceptin/orphanin FQ (NOP) receptor. J Med Chem. 2012 Jun 14;55(11):4955-67. doi: 10.1021/jm201629q. PubMed PMID: 22541041.

11: Cannarsa R, Carretta D, Lattanzio F, Candeletti S, Romualdi P. ∆(9)-Tetrahydrocannabinol decreases NOP receptor density and mRNA levels in human SH-SY5Y cells. J Mol Neurosci. 2012 Feb;46(2):285-92. doi: 10.1007/s12031-011-9552-0. PubMed PMID: 21603976.

12: Saccone PA, Zelenock KA, Lindsey AM, Sulima A, Rice KC, Prinssen EP, Wichmann J, Woods JH. Characterization of the Discriminative Stimulus Effects of a NOP Receptor Agonist Ro 64-6198 in Rhesus Monkeys. J Pharmacol Exp Ther. 2016 Apr;357(1):17-23. doi: 10.1124/jpet.115.231134. PubMed PMID: 26801398; PubMed Central PMCID: PMC4809320.

13: Sukhtankar DD, Lagorio CH, Ko MC. Effects of the NOP agonist SCH221510 on producing and attenuating reinforcing effects as measured by drug self-administration in rats. Eur J Pharmacol. 2014 Dec 15;745:182-9. doi: 10.1016/j.ejphar.2014.10.029. PubMed PMID: 25446568; PubMed Central PMCID: PMC4259829.

14: Fassini A, Scopinho AA, Resstel LB, Corrêa FM. NOP receptors in the prelimbic cortex have an inhibitory influence on cardiovascular responses induced by restraint stress. Neuropeptides. 2016 Jun;57:35-44. doi: 10.1016/j.npep.2016.02.006. PubMed PMID: 26935148.

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17: Rutten K, De Vry J, Bruckmann W, Tzschentke TM. Pharmacological blockade or genetic knockout of the NOP receptor potentiates the rewarding effect of morphine in rats. Drug Alcohol Depend. 2011 Apr 1;114(2-3):253-6. doi: 10.1016/j.drugalcdep.2010.10.004. PubMed PMID: 21095077.

18: Carvalho D, Petronilho F, Vuolo F, Machado RA, Constantino L, Guerrini R, Calo G, Gavioli EC, Streck EL, Dal-Pizzol F. The nociceptin/orphanin FQ-NOP receptor antagonist effects on an animal model of sepsis. Intensive Care Med. 2008 Dec;34(12):2284-90. doi: 10.1007/s00134-008-1313-3. PubMed PMID: 18846364.

19: Cippitelli A, Schoch J, Debevec G, Brunori G, Zaveri NT, Toll L. A key role for the N/OFQ-NOP receptor system in modulating nicotine taking in a model of nicotine and alcohol co-administration. Sci Rep. 2016 May 20;6:26594. doi: 10.1038/srep26594. PubMed PMID: 27199205; PubMed Central PMCID: PMC4873733.

20: Liao YY, Trapella C, Chiou LC. 1-Benzyl-N-[3-[spiroisobenzofuran-1(3H),4'-piperidin-1-yl]propyl]pyrrolidine-2-ca rboxamide (Compound 24) antagonizes NOP receptor-mediated potassium channel activation in rat periaqueductal gray slices. Eur J Pharmacol. 2009 Mar 15;606(1-3):84-9. doi: 10.1016/j.ejphar.2009.01.036. PubMed PMID: 19374842.