WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 531976
CAS#: 256640-45-6
Description: J-113397 is a potent and selective NOP receptor antagonist (IC50 values are 2.3, 1400, 2200 and > 10000 nM for NOP, κ, μ and δ-opioid receptors respectively). J-113397 inhibits nociceptin/orphanin FQ-induced hyperalgesia in the mouse tail-flick test.
MedKoo Cat#: 531976
Name: J-113397
CAS#: 256640-45-6
Chemical Formula: C24H37N3O2
Exact Mass: 399.2886
Molecular Weight: 399.58
Elemental Analysis: C, 72.14; H, 9.33; N, 10.52; O, 8.01
This product is not in stock, which may be available by custom synthesis.
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Synonym: J-113397; J 113397; J113397.
IUPAC/Chemical Name: 1-[(3R,4R)-1-(cyclooctylmethyl)-3-(hydroxymethyl)piperidin-4-yl]-3-ethylbenzimidazol-2-one
InChi Key: MBGVUMXBUGIIBQ-LEWJYISDSA-N
InChi Code: InChI=1S/C24H37N3O2/c1-2-26-22-12-8-9-13-23(22)27(24(26)29)21-14-15-25(17-20(21)18-28)16-19-10-6-4-3-5-7-11-19/h8-9,12-13,19-21,28H,2-7,10-11,14-18H2,1H3/t20-,21+/m0/s1
SMILES Code: O=C1N(CC)C2=CC=CC=C2N1[C@H]3[C@H](CO)CN(CC4CCCCCCC4)CC3
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
The following data is based on the product molecular weight 399.58 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: Scoto GM, Aricò G, Ronsisvalle S, Parenti C. Effects of intraplantar nocistatin and (±)-J 113397 injections on nociceptive behavior in a rat model of inflammation. Pharmacol Biochem Behav. 2012 Jan;100(3):639-44. doi: 10.1016/j.pbb.2011.11.007. PubMed PMID: 22120202.
2: Visanji NP, de Bie RM, Johnston TH, McCreary AC, Brotchie JM, Fox SH. The nociceptin/orphanin FQ (NOP) receptor antagonist J-113397 enhances the effects of levodopa in the MPTP-lesioned nonhuman primate model of Parkinson's disease. Mov Disord. 2008 Oct 15;23(13):1922-5. doi: 10.1002/mds.22086. PubMed PMID: 18759357.
3: Smith ED, Ariane Vinson N, Zhong D, Berrang BD, Catanzaro JL, Thomas JB, Navarro HA, Gilmour BP, Deschamps J, Carroll FI. A new synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro- 2H-benzimidazol-2-one (J-113397) and activity in a calcium mobilization assay. Bioorg Med Chem. 2008 Jan 15;16(2):822-9. PubMed PMID: 17976996; PubMed Central PMCID: PMC2323199.
4: Marti M, Trapella C, Viaro R, Morari M. The nociceptin/orphanin FQ receptor antagonist J-113397 and L-DOPA additively attenuate experimental parkinsonism through overinhibition of the nigrothalamic pathway. J Neurosci. 2007 Feb 7;27(6):1297-307. PubMed PMID: 17287504.
5: Trapella C, Guerrini R, Piccagli L, Calo' G, Carra' G, Spagnolo B, Rubini S, Fanton G, Hebbes C, McDonald J, Lambert DG, Regoli D, Salvadori S. Identification of an achiral analogue of J-113397 as potent nociceptin/orphanin FQ receptor antagonist. Bioorg Med Chem. 2006 Feb 1;14(3):692-704. PubMed PMID: 16202610.
6: Chiou LC, Fan SH. CompB (J-113397), selectively and competitively antagonizes nociceptin activation of inwardly rectifying K(+) channels in rat periaqueductal gray slices. Neuropharmacology. 2002 Jun;42(7):987-92. PubMed PMID: 12069909.
7: De Risi C, Piero Pollini G, Trapella C, Peretto I, Ronzoni S, Giardina GA. A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-be nzimidazol-2-one(J-113397), the first non-peptide ORL-1 receptor antagonist.. Bioorg Med Chem. 2001 Jul;9(7):1871-7. PubMed PMID: 11425589.
8: Ichikawa D, Ozaki S, Azuma T, Nambu H, Kawamoto H, Iwasawa Y, Takeshima H, Ohta H. In vitro inhibitory effects of J-113397 on nociceptin/orphanin FQ-stimulated. Neuroreport. 2001 Jun 13;12(8):1757-61. PubMed PMID: 11409754.
9: Ozaki S, Kawamoto H, Itoh Y, Miyaji M, Azuma T, Ichikawa D, Nambu H, Iguchi T, Iwasawa Y, Ohta H. In vitro and in vivo pharmacological characterization of J-113397, a potent and selective non-peptidyl ORL1 receptor antagonist. Eur J Pharmacol. 2000 Aug 18;402(1-2):45-53. PubMed PMID: 10940356.
10: Bigoni R, Calo' G, Rizzi A, Guerrini R, De Risi C, Hashimoto Y, Hashiba E, Lambert DG, Regoli D. In vitro characterization of J-113397, a non-peptide nociceptin/orphanin FQ receptor antagonist. Naunyn Schmiedebergs Arch Pharmacol. 2000 May;361(5):565-8. PubMed PMID: 10832612.
11: Ozaki S, Kawamoto H, Itoh Y, Miyaji M, Iwasawa Y, Ohta H. A potent and highly selective nonpeptidyl nociceptin/orphanin FQ receptor (ORL1) antagonist: J-113397. Eur J Pharmacol. 2000 Jan 17;387(3):R17-8. PubMed PMID: 10650183.
12: Kawamoto H, Ozaki S, Itoh Y, Miyaji M, Arai S, Nakashima H, Kato T, Ohta H, Iwasawa Y. Discovery of the first potent and selective small molecule opioid receptor-like (ORL1) antagonist: 1-[(3R,4R)-1-cyclooctylmethyl-3- hydroxymethyl-4-piperidyl]-3-ethyl-1, 3-dihydro-2H-benzimidazol-2-one (J-113397). J Med Chem. 1999 Dec 16;42(25):5061-3. PubMed PMID: 10602690.
