A partial agonist for α4β2 subunit-containing nAChRs
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TC 2559 (fumarate)

Item No. 25600

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(5-ethoxy-3-pyridinyl)-N-methyl-3-buten-1-amine, difumaric acid
CAS Number
212332-35-9
Molecular Formula
C12H18N2O • 2C4H4O4
Formula Weight
438.4
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
CNCC/C=C/C1=CC(OCC)=CN=C1.OC(/C=C/C(O)=O)=O.OC(/C=C\C(O)=O)=O
InChi Code
InChI=1S/C12H18N2O.2C4H4O4/c1-3-15-12-8-11(9-14-10-12)6-4-5-7-13-2;2*5-3(6)1-2-4(7)8/h4,6,8-10,13H,3,5,7H2,1-2H3;2*1-2H,(H,5,6)(H,7,8)/b6-4+;2*2-1+
InChi Key
GEWVPSJQGJBDLM-MYBAKCFCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $153

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    10 mg

    $253

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    25 mg

    $587

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    Product Description

    TC 2559 is a CNS-selective partial agonist for α4β2 subunit-containing nicotinic acetylcholine receptors (nAChRs) with an EC50 value of 0.18 µM for calcium signaling in HEK293 cells expressing human recombinant nAChRs.1,2 It is selective for α4β2 over α2β4, α4β4, α3β4, α3β2, and α7 subunit-containing nAChRs (EC50s = 14, 12.5, >30, >100, and >100 µM, respectively). It increases dopamine cell firing in the rat ventral tegmental area (VTA) in vitro. TC 2559 increases spontaneous inhibitory postsynaptic currents (sIPSCs) in dorsal horn neurons, indicating an enhancement of inhibitory synaptic transmission, an effect that is blocked by the α4β2 subunit-containing nAChR antagonist DHβE.3 It reduces formalin-induced paw-licking time in mice when administered at doses of 3 and 10 mg/kg and increases paw withdrawal latency in a rat model of chronic constriction injury when administered at a dose of 3 mg/kg. TC 2559 (3 and 6 µmol/kg) also reverses cognitive deficits induced by scopolamine in rats, increasing step-through latency in a passive avoidance task.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bencherif, M., Bane, A.J., Miller, C.H., et al. TC-2559: A novel orally active ligand selective at neuronal acetylcholine receptors. Eur. J. Pharmacol. 409(1), 45-55 (2000).

    2. Chen, Y., Sharples, T.J.W., Phillips, K.G., et al. The nicotinic α4β2 receptor selective agonist, TC-2559, increases dopamine neuronal activity in the ventral tegmental area of rat midbrain slices. Neuropharmacology 45(3), 334-344 (2003).

    3. Cheng, L.-Z., Han, L., Fan, J., et al. Enhanced inhibitory synaptic transmission in the spinal dorsal horn mediates antinociceptive effects of TC-2559. Mol. Pain 7:56, (2011).