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MedKoo Cat#: 526265 | Name: SB 224289

Description:

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

SB 224289 is a selective 5-HT1B receptor antagonist (pKi = 8.2). SB 224289 displays > 60-fold selectivity over 5-HT1D, 5-HT1A, 5-HT1E, 5-HT1F, 5-HT2A and 5-HT2C receptors in radioligand binding and functional assays. SB 224289 is a centrally active following oral administration in vivo.

Chemical Structure

SB 224289
SB 224289
CAS#180083-23-2

Theoretical Analysis

MedKoo Cat#: 526265

Name: SB 224289

CAS#: 180083-23-2

Chemical Formula: C32H32N4O3

Exact Mass: 520.2474

Molecular Weight: 520.63

Elemental Analysis: C, 73.82; H, 6.20; N, 10.76; O, 9.22

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
SB 224289; SB224289; SB-224289.
IUPAC/Chemical Name
(1'-Methyl-6,7-dihydro-5H-spiro(furo(2,3-f)indole-3,4'-piperidin)-5-yl)(2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methanone
InChi Key
ATQMRMGXINTJHV-UHFFFAOYSA-N
InChi Code
InChI=1S/C32H32N4O3/c1-20-16-25(30-33-21(2)39-34-30)8-9-26(20)22-4-6-23(7-5-22)31(37)36-13-10-24-17-29-27(18-28(24)36)32(19-38-29)11-14-35(3)15-12-32/h4-9,16-18H,10-15,19H2,1-3H3
SMILES Code
O=C(N1CCC2=C1C=C3C(OCC34CCN(C)CC4)=C2)C5=CC=C(C6=CC=C(C7=NOC(C)=N7)C=C6C)C=C5
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

Preparing Stock Solutions

The following data is based on the product molecular weight 520.63 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
1: Cassilly CD, Maddox MM, Cherian PT, Bowling JJ, Hamann MT, Lee RE, Reynolds TB. SB-224289 Antagonizes the Antifungal Mechanism of the Marine Depsipeptide Papuamide A. PLoS One. 2016 May 16;11(5):e0154932. doi: 10.1371/journal.pone.0154932. PMID: 27183222; PMCID: PMC4868317. 2: Selkirk JV, Scott C, Ho M, Burton MJ, Watson J, Gaster LM, Collin L, Jones BJ, Middlemiss DN, Price GW. SB-224289--a novel selective (human) 5-HT1B receptor antagonist with negative intrinsic activity. Br J Pharmacol. 1998 Sep;125(1):202-8. doi: 10.1038/sj.bjp.0702059. PMID: 9776361; PMCID: PMC1565605. 3: Hoplight BJ, Vincow ES, Neumaier JF. The effects of SB 224289 on anxiety and cocaine-related behaviors in a novel object task. Physiol Behav. 2005 Apr 13;84(5):707-14. doi: 10.1016/j.physbeh.2005.02.016. Epub 2005 Apr 13. PMID: 15885246. 4: Meneses A. Could the 5-HT1B receptor inverse agonism affect learning consolidation? Neurosci Biobehav Rev. 2001 Mar;25(2):193-201. doi: 10.1016/s0149-7634(01)00007-0. PMID: 11323083. 5: Shalom G, Gur E, Van de Kar LD, Newman ME. Repeated administration of the 5-HT(1B) receptor antagonist SB-224289 blocks the desensitisation of 5-HT(1B) autoreceptors induced by fluoxetine in rat frontal cortex. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):84-90. doi: 10.1007/s00210-004-0958-x. Epub 2004 Aug 12. PMID: 15309378. 6: Sánchez-Maldonado C, López-Sánchez P, Anguiano-Robledo L, Leopoldo M, Lacivita E, Terrón JA. GR-127935-sensitive mechanism mediating hypotension in anesthetized rats: are 5-HT5B receptors involved? J Cardiovasc Pharmacol. 2015 Apr;65(4):335-41. doi: 10.1097/FJC.0000000000000200. PMID: 25502305. 7: Maximino C, Puty B, Benzecry R, Araújo J, Lima MG, de Jesus Oliveira Batista E, Renata de Matos Oliveira K, Crespo-Lopez ME, Herculano AM. Role of serotonin in zebrafish (Danio rerio) anxiety: relationship with serotonin levels and effect of buspirone, WAY 100635, SB 224289, fluoxetine and para- chlorophenylalanine (pCPA) in two behavioral models. Neuropharmacology. 2013 Aug;71:83-97. doi: 10.1016/j.neuropharm.2013.03.006. Epub 2013 Mar 28. PMID: 23541719. 8: Gaster LM, Ham P, Joiner GF, King FD, Mulholland KR, Wyman PA, Hagan JJ, Price GW, Roberts C, Routledge C, Selkirk J, Slade PD, Middlemiss DN. The selective 5-HT1B receptor inverse agonist SB-224289, potently blocks terminal 5-HT autoreceptor function both in vitro and in vivo. Ann N Y Acad Sci. 1998 Dec 15;861:270-1. doi: 10.1111/j.1749-6632.1998.tb10219.x. PMID: 9928285. 9: Gaster LM, Blaney FE, Davies S, Duckworth DM, Ham P, Jenkins S, Jennings AJ, Joiner GF, King FD, Mulholland KR, Wyman PA, Hagan JJ, Hatcher J, Jones BJ, Middlemiss DN, Price GW, Riley G, Roberts C, Routledge C, Selkirk J, Slade PD. The selective 5-HT1B receptor inverse agonist 1'-methyl-5-[[2'-methyl-4'-(5-methyl-1,2, 4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydro- spiro[furo[2,3-f]indole-3,4'-piperidine] (SB-224289) potently blocks terminal 5-HT autoreceptor function both in vitro and in vivo. J Med Chem. 1998 Apr 9;41(8):1218-35. doi: 10.1021/jm970457s. PMID: 9548813. 10: Roberts C, Price GW, Middlemiss DN. Ligands for the investigation of 5-HT autoreceptor function. Brain Res Bull. 2001 Nov 15;56(5):463-9. doi: 10.1016/s0361-9230(01)00628-1. PMID: 11750791. 11: Cervantes-Durán C, Rocha-González HI, Granados-Soto V. Peripheral and spinal 5-HT receptors participate in the pronociceptive and antinociceptive effects of fluoxetine in rats. Neuroscience. 2013 Nov 12;252:396-409. doi: 10.1016/j.neuroscience.2013.08.022. Epub 2013 Aug 27. PMID: 23994595. 12: Budrow C, Elder K, Coyle M, Centner A, Lipari N, Cohen S, Glinski J, Kinzonzi N, Wheelis E, McManus G, Manfredsson F, Bishop C. Broad Serotonergic Actions of Vortioxetine as a Promising Avenue for the Treatment of L-DOPA- Induced Dyskinesia. Cells. 2023 Mar 8;12(6):837. doi: 10.3390/cells12060837. PMID: 36980178; PMCID: PMC10047495. 13: Stenfors C, Ross SB. Failure to detect in vivo inverse agonism of the 5-HT(1B) receptor antagonist SB-224289 in 5-HT-depleted guinea-pigs. Naunyn Schmiedebergs Arch Pharmacol. 2002 Jun;365(6):462-7. doi: 10.1007/s00210-002-0564-8. Epub 2002 Apr 18. PMID: 12070760. 14: Quiñonez-Bastidas GN, Pineda-Farias JB, Flores-Murrieta FJ, Rodríguez- Silverio J, Reyes-García JG, Godínez-Chaparro B, Granados-Soto V, Rocha-González HI. Antinociceptive effect of (-)-epicatechin in inflammatory and neuropathic pain in rats. Behav Pharmacol. 2018 Apr;29(2 and 3-Spec Issue):270-279. doi: 10.1097/FBP.0000000000000320. PMID: 28590304. 15: Yang Y, Zhang L, Yu J, Ma Z, Li M, Wang J, Hu P, Zou J, Liu X, Liu Y, An S, Xiang C, Guo X, Hao Q, Xu TR. A Novel 5-HT1B Receptor Agonist of Herbal Compounds and One of the Therapeutic Uses for Alzheimer's Disease. Front Pharmacol. 2021 Sep 6;12:735876. doi: 10.3389/fphar.2021.735876. PMID: 34552493; PMCID: PMC8450432. 16: Roberts C, Allen L, Langmead CJ, Hagan JJ, Middlemiss DN, Price GW. The effect of SB-269970, a 5-HT(7) receptor antagonist, on 5-HT release from serotonergic terminals and cell bodies. Br J Pharmacol. 2001 Apr;132(7):1574-80. doi: 10.1038/sj.bjp.0703979. PMID: 11264252; PMCID: PMC1572709. 17: Vidal-Cantú GC, Jiménez-Hernández M, Rocha-González HI, Villalón CM, Granados-Soto V, Muñoz-Islas E. Role of 5-HT5A and 5-HT1B/1D receptors in the antinociception produced by ergotamine and valerenic acid in the rat formalin test. Eur J Pharmacol. 2016 Jun 15;781:109-16. doi: 10.1016/j.ejphar.2016.04.009. Epub 2016 Apr 8. PMID: 27068146. 18: Godínez-Chaparro B, López-Santillán FJ, Argüelles CF, Villalón CM, Granados- Soto V. Role of 5-HT₁B/₁D receptors in the reduction of formalin-induced nociception and secondary allodynia/hyperalgesia produced by antimigraine drugs in rats. Life Sci. 2013 Jun 13;92(22):1046-54. doi: 10.1016/j.lfs.2013.03.023. Epub 2013 Apr 9. PMID: 23583574. 19: Roberts C, Price GW, Gaster L, Jones BJ, Middlemiss DN, Routledge C. Importance of h5-HT1B receptor selectivity for 5-HT terminal autoreceptor activity: an in vivo microdialysis study in the freely-moving guinea-pig. Neuropharmacology. 1997 Apr-May;36(4-5):549-57. doi: 10.1016/s0028-3908(97)00026-9. PMID: 9225280. 20: Nagata A, Nakayama K, Nakamura S, Mochizuki A, Gemba C, Aoki R, Dantsuji M, Maki K, Inoue T. Serotonin1B receptor-mediated presynaptic inhibition of proprioceptive sensory inputs to jaw-closing motoneurons. Brain Res Bull. 2019 Jul;149:260-267. doi: 10.1016/j.brainresbull.2019.05.001. Epub 2019 May 7. PMID: 31075304.