TC-2559 free base | CAS#189274-78-0 | antinociceptive

MedKoo Cat#: 585257 | Name: TC-2559 free base

Description:

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

TC-2559 is a selective agonist for the α4β2 nicotinic acetylcholine receptor (nAChR) subtype. In vitro studies have demonstrated that TC-2559 exhibits high affinity and selectivity for α4β2 nAChRs, with minimal activity at other nAChR subtypes. In vivo experiments have shown that TC-2559 can enhance cognitive performance in animal models, suggesting potential therapeutic applications for cognitive disorders.

Chemical Structure

TC-2559 free base

CAS#189274-78-0 (free base),

Theoretical Analysis

MedKoo Cat#: 585257

Name: TC-2559 free base

CAS#: 189274-78-0 (free base),

Chemical Formula: C12H18N2O

Exact Mass: 206.1419

Molecular Weight: 206.29

Elemental Analysis: C, 69.87; H, 8.80; N, 13.58; O, 7.76

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 #

189274-78-0 (free base) 2454492-41-0 (fumarate)

Synonym

TC 2559; TC2559; TC-2559

IUPAC/Chemical Name

3-Buten-1-amine, 4-(5-ethoxy-3-pyridinyl)-N-methyl-, (3E)-

InChi Key

HFZDMKMXPGRKCK-GQCTYLIASA-N

InChi Code

InChI=1S/C12H18N2O/c1-3-15-12-8-11(9-14-10-12)6-4-5-7-13-2/h4,6,8-10,13H,3,5,7H2,1-2H3/b6-4+

SMILES Code

CNCC/C=C/C1=CC(OCC)=CN=C1O

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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 206.29 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.

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: Mondragón-García A, Ramírez-Sánchez E, Francia-Ramírez D, Hernández-González O, Rojano-Posada Y, Ortega-Tinoco S, Garduño J, Verdugo-Díaz L, Hernández-López S. S-(+)-mecamylamine increases the firing rate of serotonin neurons and diminishes depressive-like behaviors in an animal model of stress. Neuroscience. 2024 Dec 6;562:75-89. doi: 10.1016/j.neuroscience.2024.10.043. Epub 2024 Oct 24. PMID: 39454712. 2: Deba F, Munoz K, Peredia E, Akk G, Hamouda AK. Assessing potentiation of the (α4)3(β2)2 nicotinic acetylcholine receptor by the allosteric agonist CMPI. J Biol Chem. 2022 Jan;298(1):101455. doi: 10.1016/j.jbc.2021.101455. Epub 2021 Nov 30. PMID: 34861241; PMCID: PMC8715118. 3: Saika F, Kiguchi N, Matsuzaki S, Kobayashi D, Kishioka S. Inflammatory Macrophages in the Sciatic Nerves Facilitate Neuropathic Pain Associated with Type 2 Diabetes Mellitus. J Pharmacol Exp Ther. 2019 Mar;368(3):535-544. doi: 10.1124/jpet.118.252668. Epub 2019 Jan 2. PMID: 30602591. 4: Kiguchi N, Kobayashi D, Saika F, Matsuzaki S, Kishioka S. Inhibition of peripheral macrophages by nicotinic acetylcholine receptor agonists suppresses spinal microglial activation and neuropathic pain in mice with peripheral nerve injury. J Neuroinflammation. 2018 Mar 27;15(1):96. doi: 10.1186/s12974-018-1133-5. PMID: 29587798; PMCID: PMC5872578. 5: Li W, Cai J, Wang BH, Huang L, Fan J, Wang Y. Antinociceptive effects of novel epibatidine analogs through activation of α4β2 nicotinic receptors. Sci China Life Sci. 2018 Jun;61(6):688-695. doi: 10.1007/s11427-017-9062-3. Epub 2018 Feb 2. PMID: 29435707. 6: Leung J, McPhee DM, Renda A, Penty N, Farhoomand F, Nashmi R, Delaney KR. MeCP2-deficient mice have reduced α4 and α6 nicotinic receptor mRNA and altered behavioral response to nicotinic agonists. Behav Brain Res. 2017 Jul 14;330:118-126. doi: 10.1016/j.bbr.2017.05.021. Epub 2017 May 12. PMID: 28506623. 7: Indurthi DC, Lewis TM, Ahring PK, Balle T, Chebib M, Absalom NL. Ligand Binding at the 4-4 Agonist-Binding Site of the 42 nAChR Triggers Receptor Activation through a Pre-Activated Conformational State. PLoS One. 2016 Aug 23;11(8):e0161154. doi: 10.1371/journal.pone.0161154. Erratum in: PLoS One. 2016 Oct 19;11(10):e0165184. doi: 10.1371/journal.pone.0165184. PMID: 27552221; PMCID: PMC4995024. 8: Kiguchi N, Saika F, Kobayashi Y, Ko MC, Kishioka S. TC-2559, an α4β2 nicotinic acetylcholine receptor agonist, suppresses the expression of CCL3 and IL-1β through STAT3 inhibition in cultured murine macrophages. J Pharmacol Sci. 2015 Jun;128(2):83-6. doi: 10.1016/j.jphs.2015.04.009. Epub 2015 May 8. PMID: 26012743. 9: Mazzaferro S, Gasparri F, New K, Alcaino C, Faundez M, Iturriaga Vasquez P, Vijayan R, Biggin PC, Bermudez I. Non-equivalent ligand selectivity of agonist sites in (α4β2)2α4 nicotinic acetylcholine receptors: a key determinant of agonist efficacy. J Biol Chem. 2014 Aug 1;289(31):21795-806. doi: 10.1074/jbc.M114.555136. Epub 2014 Jun 16. PMID: 24936069; PMCID: PMC4118137. 10: Papke RL, Stokes C, Muldoon P, Imad Damaj M. Similar activity of mecamylamine stereoisomers in vitro and in vivo. Eur J Pharmacol. 2013 Nov 15;720(1-3):264-75. doi: 10.1016/j.ejphar.2013.10.018. Epub 2013 Oct 23. PMID: 24161916; PMCID: PMC3992716. 11: Cheng LZ, Han L, Fan J, Huang LT, Peng LC, Wang Y. Enhanced inhibitory synaptic transmission in the spinal dorsal horn mediates antinociceptive effects of TC-2559. Mol Pain. 2011 Aug 4;7:56. doi: 10.1186/1744-8069-7-56. PMID: 21816108; PMCID: PMC3161881. 12: Loomis S, Gilmour G. Corticosterone urinalysis and nicotinic receptor modulation in rats. J Neurosci Methods. 2010 May 15;188(2):243-9. doi: 10.1016/j.jneumeth.2010.02.016. Epub 2010 Feb 19. PMID: 20171986. 13: Moore C, Wang Y, Ramage AG. Cardiovascular effects of activation of central alpha7 and alpha4beta2 nAChRs: a role for vasopressin in anaesthetized rats. Br J Pharmacol. 2008 Apr;153(8):1728-38. doi: 10.1038/bjp.2008.47. Epub 2008 Feb 25. PMID: 18297099; PMCID: PMC2438263. 14: Lippiello P, Letchworth SR, Gatto GJ, Traina VM, Bencherif M. Ispronicline: a novel alpha4beta2 nicotinic acetylcholine receptor-selective agonist with cognition-enhancing and neuroprotective properties. J Mol Neurosci. 2006;30(1-2):19-20. doi: 10.1385/JMN:30:1:19. PMID: 17192610. 15: Smith JW, Mogg A, Tafi E, Peacey E, Pullar IA, Szekeres P, Tricklebank M. Ligands selective for alpha4beta2 but not alpha3beta4 or alpha7 nicotinic receptors generalise to the nicotine discriminative stimulus in the rat. Psychopharmacology (Berl). 2007 Feb;190(2):157-70. doi: 10.1007/s00213-006-0596-8. Epub 2006 Nov 18. PMID: 17115136. 16: Wang Y, Sherwood JL, Lodge D. The alpha4beta2 nicotinic acetylcholine receptor agonist TC-2559 impairs long-term potentiation in the dentate gyrus in vivo. Neurosci Lett. 2006 Oct 9;406(3):183-8. doi: 10.1016/j.neulet.2006.06.075. Epub 2006 Aug 28. PMID: 16935422. 17: Moroni M, Zwart R, Sher E, Cassels BK, Bermudez I. alpha4beta2 nicotinic receptors with high and low acetylcholine sensitivity: pharmacology, stoichiometry, and sensitivity to long-term exposure to nicotine. Mol Pharmacol. 2006 Aug;70(2):755-68. doi: 10.1124/mol.106.023044. Epub 2006 May 23. PMID: 16720757. 18: Zwart R, Broad LM, Xi Q, Lee M, Moroni M, Bermudez I, Sher E. 5-I A-85380 and TC-2559 differentially activate heterologously expressed alpha4beta2 nicotinic receptors. Eur J Pharmacol. 2006 Jun 6;539(1-2):10-7. doi: 10.1016/j.ejphar.2006.03.077. Epub 2006 Apr 5. PMID: 16674940. 19: Wang Y, Sherwood JL, Miles CP, Whiffin G, Lodge D. TC-2559 excites dopaminergic neurones in the ventral tegmental area by stimulating alpha4beta2-like nicotinic acetylcholine receptors in anaesthetised rats. Br J Pharmacol. 2006 Feb;147(4):379-90. doi: 10.1038/sj.bjp.0706621. PMID: 16402043; PMCID: PMC1616994. 20: Chen Y, Sharples TJ, Phillips KG, Benedetti G, Broad LM, Zwart R, Sher E. The nicotinic alpha 4 beta 2 receptor selective agonist, TC-2559, increases dopamine neuronal activity in the ventral tegmental area of rat midbrain slices. Neuropharmacology. 2003 Sep;45(3):334-44. doi: 10.1016/s0028-3908(03)00189-8. PMID: 12871651.