An orally-available 5-HT6 antagonist
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SB-271046 (hydrochloride)

Item No. 18513

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-chloro-N-[4-methoxy-3-(1-piperazinyl)phenyl]-3-methyl-benzo[b]thiophene-2-sulfonamide, monohydrochloride
CAS Number
209481-24-3
Molecular Formula
C20H22ClN3O3S2 • HCl
Formula Weight
488.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 10 mg/mlDMSO:PBS(pH 7.2) (1:4): 0.2 mg/ml
λmax
211, 241, 282 nm
SMILES
ClC1=CC=C2C(C(C)=C(S(NC3=CC(N4CCNCC4)=C(OC)C=C3)(=O)=O)S2)=C1.Cl
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
InChi Key
RMXZRJYGJMSDQK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $90

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    10 mg

    $168

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    25 mg

    $392

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    50 mg

    $696

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    Product Description

    SB-271046 is an orally-available antagonist of the serotonin (5-hydroxytryptamine, or 5-HT; Item No. 14332) receptor 5-HT6 (pKi = 9.02-8.92).1,2 It is at least 100-fold selective for 5-HT6 over other 5-HT receptors, as well as 55 other receptors, enzymes, and ion channels.2 While it does not alter basal levels of 5-HT, dopamine, or noradrenaline, SB-271046 produces a significant increase in extracellular levels of glutamate and aspartate within the frontal cortex.3 It has been used to evaluate the role of 5-HT6 in learning and memory.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bromidge, S.M., Brown, A.M., Clarke, S.E., et al. 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. 42(2), 202-205 (1999).

    2. Routledge, C., Bromidge, S.M., Moss, S.F., et al. Characterization of SB-271046: A potent, selective and orally active 5-HT6 receptor antagonist. Br. J. Pharmacol. 130, 1606-1612 (2000).

    3. Dawson, L.A., Nguyen, H.Q., and 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. 130, 23-26 (2000).

    4. Woods, S., Clarke, N.N., Layfield, R., et al. 5-HT(6) receptor agonists and antagonists enhance learning and memory in a conditioned emotion response paradigm by modulation of cholinergic and glutamatergic mechanisms. Br. J. Pharmacol. 167, 436-449 (2012).