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MedKoo Cat#: 526698 | Name: SB271046 HCl
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Description:

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

SB 271046 is one of the first selective 5-HT6 receptor antagonists to be discovered. SB 271046 was found to be potent and selective in vitro and had good oral bioavailability in vivo, but had poor penetration across the blood–brain barrier. SB 271046 was found to increase levels of the excitatory amino acid neurotransmitters glutamate and aspartate, as well as dopamine and noradrenaline in the frontal cortex and hippocampus of rats, and 5-HT6 antagonists have been shown to produce nootropic effects in a variety of animal studies. Suggested applications of these drugs include treatment of schizophrenia and other psychiatric disorders.

Chemical Structure

SB271046 HCl
SB271046 HCl
CAS#209481-24-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 526698

Name: SB271046 HCl

CAS#: 209481-24-3 (HCl)

Chemical Formula: C20H23Cl2N3O3S2

Exact Mass: 0.0000

Molecular Weight: 488.44

Elemental Analysis: C, 49.18; H, 4.75; Cl, 14.52; N, 8.60; O, 9.83; S, 13.13

Price and Availability

Size Price Availability Quantity
5mg USD 375.00 2 Weeks
10mg USD 575.00 2 Weeks
25mg USD 875.00 2 Weeks
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Related CAS #
209481-24-3 (HCl) 209481-20-9 (free base)
Synonym
SB-271046; SB 271046; SB271046; SB-271046 HCl; SB-271046 hydrochloride; SB 271046A;
IUPAC/Chemical Name
5-chloro-N-(4-methoxy-3-piperazin-1-ylphenyl)-3-methyl-1-benzothiophene-2-sulfonamide hydrochloride
InChi Key
RMXZRJYGJMSDQK-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H22ClN3O3S2.ClH/c1-13-16-11-14(21)3-6-19(16)28-20(13)29(25,26)23-15-4-5-18(27-2)17(12-15)24-9-7-22-8-10-24;/h3-6,11-12,22-23H,7-10H2,1-2H3;1H
SMILES Code
O=S(C1=C(C)C2=CC(Cl)=CC=C2S1)(NC3=CC=C(OC)C(N4CCNCC4)=C3)=O.[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, 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
Related CAS# 209481-24-3 ( SB-271046 HCl); 209481-20-9 ( SB-271046 free base).
Product Data
Product Data
Instruction
View handling instruction
Biological target:
SB 271046 HCl is a selective, orally active 5-HT6 antagonist (with pKi values of 9.02-8.92, 6.55, 6.35, 6.27, 6.05, 5.95, 5.76, 5.73, 5.62, 5.55, 5.41, 5.39, 5.27 and < 4.99 at 5-HT6, 5-HT1D, 5-HT1A, D3, 5-HT1B, 5-HT1F, α1B, 5-HT2C, 5-HT2A, D2, 5-HT2B, 5-HT7, 5-HT4 and 5-HT1E, respectively) and is > 200-fold selective over 55 other receptors, enzymes and ion channels. SB 271046 HCl increases extracellular glutamate and aspartate in the frontal cortex, and exhibits anticonvulsant activity (EC50 = 0.16 μM).
In vitro activity:
In Chinese hamster ovary (CHO)-Dukx and HeLa cells, SB 271046 exhibited a high affinity (K(i)=1.9 nM) for 5-HT(6) receptors compared to methiothepin, mianserin, 5-methoxytryptamine, and ritanserin. Reference: Anal Biochem. 2008 Oct 1;381(1):27-32. https://pubmed.ncbi.nlm.nih.gov/18601889/
In vivo activity:
In a rat model of nicotine addiction, the administration of SB 271046 showed a dose-dependent reduction in both the development and expression of nicotine sensitization compared to control. Reference: Neuropharmacology. 2011 Sep;61(3):451-7. https://pubmed.ncbi.nlm.nih.gov/21329711/
Solvent mg/mL mM
Solubility
DMSO 48.8 100.00
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 488.44 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. Carrick T, Kowal D, Nawoschik S, Zhang G, Chan K, Dunlop J. Development of a scintillation proximity assay binding method for the human 5-hydroxytryptamine 6 receptor using intact cells. Anal Biochem. 2008 Oct 1;381(1):27-32. doi: 10.1016/j.ab.2008.06.013. Epub 2008 Jun 13. PMID: 18601889. 2. Romero G, Sánchez E, Pujol M, Pérez P, Codony X, Holenz J, Buschmann H, Pauwels PJ. Efficacy of selective 5-HT6 receptor ligands determined by monitoring 5-HT6 receptor-mediated cAMP signaling pathways. Br J Pharmacol. 2006 Aug;148(8):1133-43. doi: 10.1038/sj.bjp.0706827. Epub 2006 Jul 24. PMID: 16865095; PMCID: PMC1752021. 3. Suárez-Santiago JE, Briones-Aranda A, Espinosa-Raya J, Picazo O. Agonist E-6837 and antagonist SB-271046 of 5-HT6 receptors both reverse the depressive-like effect induced in mice by subchronic ketamine administration. Behav Pharmacol. 2017 Oct;28(7):582-585. doi: 10.1097/FBP.0000000000000327. PMID: 28704275. 4. de Bruin NM, Kloeze BM, McCreary AC. The 5-HT₆ serotonin receptor antagonist SB-271046 attenuates the development and expression of nicotine-induced locomotor sensitisation in Wistar rats. Neuropharmacology. 2011 Sep;61(3):451-7. doi: 10.1016/j.neuropharm.2011.01.045. Epub 2011 Feb 15. PMID: 21329711.
In vitro protocol:
1. Carrick T, Kowal D, Nawoschik S, Zhang G, Chan K, Dunlop J. Development of a scintillation proximity assay binding method for the human 5-hydroxytryptamine 6 receptor using intact cells. Anal Biochem. 2008 Oct 1;381(1):27-32. doi: 10.1016/j.ab.2008.06.013. Epub 2008 Jun 13. PMID: 18601889. 2. Romero G, Sánchez E, Pujol M, Pérez P, Codony X, Holenz J, Buschmann H, Pauwels PJ. Efficacy of selective 5-HT6 receptor ligands determined by monitoring 5-HT6 receptor-mediated cAMP signaling pathways. Br J Pharmacol. 2006 Aug;148(8):1133-43. doi: 10.1038/sj.bjp.0706827. Epub 2006 Jul 24. PMID: 16865095; PMCID: PMC1752021.v
In vivo protocol:
1. Suárez-Santiago JE, Briones-Aranda A, Espinosa-Raya J, Picazo O. Agonist E-6837 and antagonist SB-271046 of 5-HT6 receptors both reverse the depressive-like effect induced in mice by subchronic ketamine administration. Behav Pharmacol. 2017 Oct;28(7):582-585. doi: 10.1097/FBP.0000000000000327. PMID: 28704275. 2. de Bruin NM, Kloeze BM, McCreary AC. The 5-HT₆ serotonin receptor antagonist SB-271046 attenuates the development and expression of nicotine-induced locomotor sensitisation in Wistar rats. Neuropharmacology. 2011 Sep;61(3):451-7. doi: 10.1016/j.neuropharm.2011.01.045. Epub 2011 Feb 15. PMID: 21329711.
1: de Bruin NM, Kloeze BM, McCreary AC. The 5-HT₆ serotonin receptor antagonist SB-271046 attenuates the development and expression of nicotine-induced locomotor sensitisation in Wistar rats. Neuropharmacology. 2011 Sep;61(3):451-7. doi: 10.1016/j.neuropharm.2011.01.045. Epub 2011 Feb 15. PubMed PMID: 21329711. 2: Foley AG, Hirst WD, Gallagher HC, Barry C, Hagan JJ, Upton N, Walsh FS, Hunter AJ, Regan CM. The selective 5-HT6 receptor antagonists SB-271046 and SB-399885 potentiate NCAM PSA immunolabeling of dentate granule cells, but not neurogenesis, in the hippocampal formation of mature Wistar rats. Neuropharmacology. 2008 Jun;54(8):1166-74. doi: 10.1016/j.neuropharm.2008.03.012. Epub 2008 Apr 1. PubMed PMID: 18455201. 3: Minabe Y, Shirayama Y, Hashimoto K, Routledge C, Hagan JJ, Ashby CR Jr. Effect of the acute and chronic administration of the selective 5-HT6 receptor antagonist SB-271046 on the activity of midbrain dopamine neurons in rats: an in vivo electrophysiological study. Synapse. 2004 Apr;52(1):20-8. PubMed PMID: 14755629. 4: Lacroix LP, Dawson LA, Hagan JJ, Heidbreder CA. 5-HT6 receptor antagonist SB-271046 enhances extracellular levels of monoamines in the rat medial prefrontal cortex. Synapse. 2004 Feb;51(2):158-64. PubMed PMID: 14618683. 5: Foley AG, Murphy KJ, Hirst WD, Gallagher HC, Hagan JJ, Upton N, Walsh FS, Regan CM. The 5-HT(6) receptor antagonist SB-271046 reverses scopolamine-disrupted consolidation of a passive avoidance task and ameliorates spatial task deficits in aged rats. Neuropsychopharmacology. 2004 Jan;29(1):93-100. PubMed PMID: 14571256. 6: Pouzet B, Didriksen M, Arnt J. Effects of the 5-HT(6) receptor antagonist, SB-271046, in animal models for schizophrenia. Pharmacol Biochem Behav. 2002 Apr;71(4):635-43. PubMed PMID: 11888555. 7: Dawson LA, Nguyen HQ, Li P. The 5-HT(6) receptor antagonist SB-271046 selectively enhances excitatory neurotransmission in the rat frontal cortex and hippocampus. Neuropsychopharmacology. 2001 Nov;25(5):662-8. PubMed PMID: 11682249. 8: Miguel-Hidalgo JJ. SB-271046 (SmithKline Beecham). Curr Opin Investig Drugs. 2001 Jan;2(1):118-22. PubMed PMID: 11527003. 9: Routledge C, Bromidge SM, Moss SF, Price GW, Hirst W, Newman H, Riley G, Gager T, Stean T, Upton N, Clarke SE, Brown AM, Middlemiss DN. Characterization of SB-271046: a potent, selective and orally active 5-HT(6) receptor antagonist. Br J Pharmacol. 2000 Aug;130(7):1606-12. PubMed PMID: 10928964; PubMed Central PMCID: PMC1572216. 10: Dawson LA, Nguyen HQ, Li P. In vivo effects of the 5-HT(6) antagonist SB-271046 on striatal and frontal cortex extracellular concentrations of noradrenaline, dopamine, 5-HT, glutamate and aspartate. Br J Pharmacol. 2000 May;130(1):23-6. PubMed PMID: 10780993; PubMed Central PMCID: PMC1572041. 11: Bromidge SM, Brown AM, Clarke SE, Dodgson K, Gager T, Grassam HL, Jeffrey PM, Joiner GF, King FD, Middlemiss DN, Moss SF, Newman H, Riley G, Routledge C, Wyman P. 5-Chloro-N-(4-methoxy-3-piperazin-1-yl- phenyl)-3-methyl-2-benzothiophenesulfon- amide (SB-271046): a potent, selective, and orally bioavailable 5-HT6 receptor antagonist. J Med Chem. 1999 Jan 28;42(2):202-5. PubMed PMID: 9925723.

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