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MedKoo Cat#: 526650 | Name: Ro 25-6981 free base

Description:

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

Ro 25-6981 is a highly potent and selective blocker of N-methyl-D-aspartate receptors containing the NR2B subunit.

Chemical Structure

Ro 25-6981 free base
Ro 25-6981 free base
CAS#169274-78-6 (free base)

Theoretical Analysis

MedKoo Cat#: 526650

Name: Ro 25-6981 free base

CAS#: 169274-78-6 (free base)

Chemical Formula: C22H29NO2

Exact Mass: 339.2198

Molecular Weight: 339.48

Elemental Analysis: C, 77.84; H, 8.61; N, 4.13; O, 9.43

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Related CAS #
169274-78-6 (free base) 1312991-76-6 (maleate) 919289-58-0 (HCl)
Synonym
Ro 25-6981; Ro25-6981; Ro-25-6981; Ro-256981; Ro 256981; Ro256981; Ro 25-6981 free base
IUPAC/Chemical Name
4-((1R,2S)-3-(4-benzylpiperidin-1-yl)-1-hydroxy-2-methylpropyl)phenol
InChi Key
WVZSEUPGUDIELE-HTAPYJJXSA-N
InChi Code
InChI=1S/C22H29NO2/c1-17(22(25)20-7-9-21(24)10-8-20)16-23-13-11-19(12-14-23)15-18-5-3-2-4-6-18/h2-10,17,19,22,24-25H,11-16H2,1H3/t17-,22+/m0/s1
SMILES Code
O[C@@H](C1=CC=C(O)C=C1)[C@@H](C)CN2CCC(CC3=CC=CC=C3)CC2
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, 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:
Ro 25-6981 inhibited 3H-MK-801 binding to rat forebrain membranes in a biphasic manner with IC50 values of 0.003 microM and 149 microM for high- (about 60%) and low-affinity sites, respectively. NMDA receptor subtypes expressed in Xenopus oocytes were blocked with IC50 values of 0.009 microM and 52 microM for the subunit combinations NR1C & NR2B and NR1C & NR2A, respectively, which indicated a >5000-fold selectivity.
In vitro activity:
Ro 25-6981 is a highly selective, activity-dependent blocker of NMDA receptors that contain the NR2B subunit. Ro 25-6981 blocked NMDA receptor subtypes in an activity-dependent manner. Ro 25-6981 protected cultured cortical neurons against glutamate toxicity and combined oxygen and glucose deprivation with IC50 values of 0.4 microM and 0.04 microM, respectively. Reference: J Pharmacol Exp Ther. 1997 Dec;283(3):1285-92. https://pubmed.ncbi.nlm.nih.gov/9400004/
In vivo activity:
Ro 25-6981 was effective against PTZ-induced seizures in infantile rats, specifically suppressing the tonic phase of the generalized tonic-clonic seizures, but it failed in juveniles. Neither sensorimotor development nor cognitive abilities and emotionality were affected by early-life exposure to Ro 25-6981. Reference: Pharmaceutics. 2021 Sep 16;13(9):1482. https://pubmed.ncbi.nlm.nih.gov/34575558/
Solvent mg/mL mM
Solubility
DMSO 100.0 294.58
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 339.48 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. Mutel V, Buchy D, Klingelschmidt A, Messer J, Bleuel Z, Kemp JA, Richards JG. In vitro binding properties in rat brain of [3H]Ro 25-6981, a potent and selective antagonist of NMDA receptors containing NR2B subunits. J Neurochem. 1998 May;70(5):2147-55. doi: 10.1046/j.1471-4159.1998.70052147.x. PMID: 9572302. 2. Fischer G, Mutel V, Trube G, Malherbe P, Kew JN, Mohacsi E, Heitz MP, Kemp JA. Ro 25-6981, a highly potent and selective blocker of N-methyl-D-aspartate receptors containing the NR2B subunit. Characterization in vitro. J Pharmacol Exp Ther. 1997 Dec;283(3):1285-92. PMID: 9400004. 3. Mareš P, Kozlová L, Mikulecká A, Kubová H. The GluN2B-Selective Antagonist Ro 25-6981 Is Effective against PTZ-Induced Seizures and Safe for Further Development in Infantile Rats. Pharmaceutics. 2021 Sep 16;13(9):1482. doi: 10.3390/pharmaceutics13091482. PMID: 34575558; PMCID: PMC8469742. 4. Szczurowska E, Mareš P. Different action of a specific NR2B/NMDA antagonist Ro 25-6981 on cortical evoked potentials and epileptic afterdischarges in immature rats. Brain Res Bull. 2015 Feb;111:1-8. doi: 10.1016/j.brainresbull.2014.11.001. Epub 2014 Nov 11. PMID: 25446739.
In vitro protocol:
1. Mutel V, Buchy D, Klingelschmidt A, Messer J, Bleuel Z, Kemp JA, Richards JG. In vitro binding properties in rat brain of [3H]Ro 25-6981, a potent and selective antagonist of NMDA receptors containing NR2B subunits. J Neurochem. 1998 May;70(5):2147-55. doi: 10.1046/j.1471-4159.1998.70052147.x. PMID: 9572302. 2. Fischer G, Mutel V, Trube G, Malherbe P, Kew JN, Mohacsi E, Heitz MP, Kemp JA. Ro 25-6981, a highly potent and selective blocker of N-methyl-D-aspartate receptors containing the NR2B subunit. Characterization in vitro. J Pharmacol Exp Ther. 1997 Dec;283(3):1285-92. PMID: 9400004.
In vivo protocol:
1. Mareš P, Kozlová L, Mikulecká A, Kubová H. The GluN2B-Selective Antagonist Ro 25-6981 Is Effective against PTZ-Induced Seizures and Safe for Further Development in Infantile Rats. Pharmaceutics. 2021 Sep 16;13(9):1482. doi: 10.3390/pharmaceutics13091482. PMID: 34575558; PMCID: PMC8469742. 2. Szczurowska E, Mareš P. Different action of a specific NR2B/NMDA antagonist Ro 25-6981 on cortical evoked potentials and epileptic after discharges in immature rats. Brain Res Bull. 2015 Feb;111:1-8. doi: 10.1016/j.brainresbull.2014.11.001. Epub 2014 Nov 11. PMID: 25446739.
1: Hume AW, Tasker RA. Endothelin-1-Induced Ischemic Damage and Functional Impairment Is Mediated Primarily by NR2B-Containing NMDA Receptors. Neurotox Res. 2020 Feb;37(2):349-355. doi: 10.1007/s12640-019-00138-3. Epub 2019 Dec 3. PMID: 31797304. 2: Busquets-Garcia A, Gomis-González M, Salgado-Mendialdúa V, Galera-López L, Puighermanal E, Martín-García E, Maldonado R, Ozaita A. Hippocampal Protein Kinase C Signaling Mediates the Short-Term Memory Impairment Induced by Delta9-Tetrahydrocannabinol. Neuropsychopharmacology. 2018 Apr;43(5):1021-1031. doi: 10.1038/npp.2017.175. Epub 2017 Aug 17. PMID: 28816239; PMCID: PMC5854793. 3: Auger ML, Floresco SB. Prefrontal cortical GABAergic and NMDA glutamatergic regulation of delayed responding. Neuropharmacology. 2017 Feb;113(Pt A):10-20. doi: 10.1016/j.neuropharm.2016.09.022. Epub 2016 Sep 24. PMID: 27678413. 4: Inta I, Domonkos E, Pfeiffer N, Sprengel R, Bettendorf M, Lang UE, Inta D, Gass P. Puberty marks major changes in the hippocampal and cortical c-Fos activation pattern induced by NMDA receptor antagonists. Neuropharmacology. 2017 Jan;112(Pt A):181-187. doi: 10.1016/j.neuropharm.2016.03.023. Epub 2016 Mar 16. PMID: 26995729. 5: Fan H, Li X, Wang W, Lai Q, Tang X, Gao D, Yin X, Xu T. Effects of NMDA- Receptor Antagonist on the Expressions of Bcl-2 and Bax in the Subventricular Zone of Neonatal Rats with Hypoxia-Ischemia Brain Damage. Cell Biochem Biophys. 2015 Nov;73(2):323-330. doi: 10.1007/s12013-015-0586-8. PMID: 27352318. 6: Fernandes A, Wojcik T, Baireddy P, Pieschl R, Newton A, Tian Y, Hong Y, Bristow L, Li YW. Inhibition of in vivo [(3)H]MK-801 binding by NMDA receptor open channel blockers and GluN2B antagonists in rats and mice. Eur J Pharmacol. 2015 Nov 5;766:1-8. doi: 10.1016/j.ejphar.2015.08.044. Epub 2015 Aug 29. PMID: 26325093. 7: Szczurowska E, Mareš P. Different action of a specific NR2B/NMDA antagonist Ro 25-6981 on cortical evoked potentials and epileptic afterdischarges in immature rats. Brain Res Bull. 2015 Feb;111:1-8. doi: 10.1016/j.brainresbull.2014.11.001. Epub 2014 Nov 11. PMID: 25446739. 8: Zhang X, Zhang Q, Tu J, Zhu Y, Yang F, Liu B, Brann D, Wang R. Prosurvival NMDA 2A receptor signaling mediates postconditioning neuroprotection in the hippocampus. Hippocampus. 2015 Mar;25(3):286-96. doi: 10.1002/hipo.22372. Epub 2014 Nov 1. PMID: 25271147. 9: Lee CH, Lü W, Michel JC, Goehring A, Du J, Song X, Gouaux E. NMDA receptor structures reveal subunit arrangement and pore architecture. Nature. 2014 Jul 10;511(7508):191-7. doi: 10.1038/nature13548. Epub 2014 Jun 22. PMID: 25008524; PMCID: PMC4263351. 10: Jiménez-Sánchez L, Campa L, Auberson YP, Adell A. The role of GluN2A and GluN2B subunits on the effects of NMDA receptor antagonists in modeling schizophrenia and treating refractory depression. Neuropsychopharmacology. 2014 Oct;39(11):2673-80. doi: 10.1038/npp.2014.123. Epub 2014 May 29. PMID: 24871546; PMCID: PMC4207347. 11: Shi WZ, Miao YL, Guo WZ, Wu W, Li BW, An LN, Fang WW, Mi WD. Leptin reverses corticosterone-induced inhibition of neural stem cell proliferation through activating the NR2B subunits of NMDA receptors. Biochem Biophys Res Commun. 2014 Apr 25;447(1):95-100. doi: 10.1016/j.bbrc.2014.03.112. Epub 2014 Mar 29. PMID: 24690172. 12: Lord B, Wintmolders C, Langlois X, Nguyen L, Lovenberg T, Bonaventure P. Comparison of the ex vivo receptor occupancy profile of ketamine to several NMDA receptor antagonists in mouse hippocampus. Eur J Pharmacol. 2013 Sep 5;715(1-3):21-5. doi: 10.1016/j.ejphar.2013.06.028. Epub 2013 Jul 16. PMID: 23872376. 13: Lima-Ojeda JM, Vogt MA, Pfeiffer N, Dormann C, Köhr G, Sprengel R, Gass P, Inta D. Pharmacological blockade of GluN2B-containing NMDA receptors induces antidepressant-like effects lacking psychotomimetic action and neurotoxicity in the perinatal and adult rodent brain. Prog Neuropsychopharmacol Biol Psychiatry. 2013 Aug 1;45:28-33. doi: 10.1016/j.pnpbp.2013.04.017. Epub 2013 Apr 30. PMID: 23643674. 14: Bortolato M, Godar SC, Melis M, Soggiu A, Roncada P, Casu A, Flore G, Chen K, Frau R, Urbani A, Castelli MP, Devoto P, Shih JC. NMDARs mediate the role of monoamine oxidase A in pathological aggression. J Neurosci. 2012 Jun 20;32(25):8574-82. doi: 10.1523/JNEUROSCI.0225-12.2012. PMID: 22723698; PMCID: PMC3417343. 15: Inta D, Lima-Ojeda JM, Dormann C, Köhr G, Sprengel R, Gass P. Combined subunit-specific and unspecific inhibition of NMDA receptors triggers distinct cortical c-fos expression patterns. Synapse. 2012 Aug;66(8):752-4. doi: 10.1002/syn.21562. Epub 2012 May 15. PMID: 22492256. 16: Spaethling J, Le L, Meaney DF. NMDA receptor mediated phosphorylation of GluR1 subunits contributes to the appearance of calcium-permeable AMPA receptors after mechanical stretch injury. Neurobiol Dis. 2012 Jun;46(3):646-54. doi: 10.1016/j.nbd.2012.03.003. Epub 2012 Mar 9. PMID: 22426393; PMCID: PMC4946953. 17: Maranis S, Stamatis D, Tsironis C, Konitsiotis S. Investigation of the antidyskinetic site of action of metabotropic and ionotropic glutamate receptor antagonists. Intracerebral infusions in 6-hydroxydopamine-lesioned rats with levodopa-induced dyskinesia. Eur J Pharmacol. 2012 May 15;683(1-3):71-7. doi: 10.1016/j.ejphar.2012.02.036. Epub 2012 Mar 4. PMID: 22410193. 18: Berretta N, Ledonne A, Mango D, Bernardi G, Mercuri NB. Hippocampus versus entorhinal cortex decoupling by an NR2 subunit-specific block of NMDA receptors in a rat in vitro model of temporal lobe epilepsy. Epilepsia. 2012 May;53(5):e80-4. doi: 10.1111/j.1528-1167.2012.03420.x. Epub 2012 Feb 23. PMID: 22360154. 19: Lemay-Clermont J, Robitaille C, Auberson YP, Bureau G, Cyr M. Blockade of NMDA receptors 2A subunit in the dorsal striatum impairs the learning of a complex motor skill. Behav Neurosci. 2011 Oct;125(5):714-23. doi: 10.1037/a0025213. PMID: 21859173. 20: Wang W, Mei XP, Wei YY, Zhang MM, Zhang T, Wang W, Xu LX, Wu SX, Li YQ. Neuronal NR2B-containing NMDA receptor mediates spinal astrocytic c-Jun N-terminal kinase activation in a rat model of neuropathic pain. Brain Behav Immun. 2011 Oct;25(7):1355-66. doi: 10.1016/j.bbi.2011.04.002. Epub 2011 Apr 7. PMID: 21496481.