GTS-21 HCl
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MedKoo CAT#: 522507

CAS#: 156223-05-1 (HCl)

Description: GTS-21, also known as DMBX-A, is a derivative of the natural product anabaseine that acts as a partial agonist at neural nicotinic acetylcholine receptors. It binds to both the α4β2 and α7 subtypes, but activates only the α7 to any significant extent. Both GTS-21 itself and its demethylated active metabolite 4-OH-GTS-21 display nootropic and neuroprotective effects, and GTS-21 is being investigated for the treatment of Alzheimer's disease, nicotine dependence, and, most significantly, for schizophrenia.


Price and Availability

Size
Price

50mg
USD 150
2g
USD 1250
Size
Price

500mg
USD 550
5g
USD 2950
Size
Price

1g
USD 850

GTS-21 HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522507
Name: GTS-21 HCl
CAS#: 156223-05-1 (HCl)
Chemical Formula: C19H22Cl2N2O2
Exact Mass: 308.15248
Molecular Weight: 381.3
Elemental Analysis: C, 59.85; H, 5.82; Cl, 18.59; N, 7.35; O, 8.39


Related CAS #: 148372-04-7 (free base)   156223-05-1 (HCl)    

Synonym: GTS-21; GTS 21; GTS21; DMBX-A

IUPAC/Chemical Name: 3-[(3E)-3-[(2,4-dimethoxyphenyl)methylidene]-5,6-dihydro-4H-pyridin-2-yl]pyridine dihydrochloride

InChi Key: BXKYFUGAAFLYJL-BXGYHSFXSA-N

InChi Code: InChI=1S/C19H20N2O2.2ClH/c1-22-17-8-7-14(18(12-17)23-2)11-15-5-4-10-21-19(15)16-6-3-9-20-13-16;;/h3,6-9,11-13H,4-5,10H2,1-2H3;2*1H/b15-11+;;

SMILES Code: COC1=CC=C(/C=C2C(C3=CC=CN=C3)=NCCC/2)C(OC)=C1.[H]Cl.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


References

1: Yue Y, Liu R, Cheng W, Hu Y, Li J, Pan X, Peng J, Zhang P. GTS-21 attenuates lipopolysaccharide-induced inflammatory cytokine production in vitro by modulating the Akt and NF-κB signaling pathway through the α7 nicotinic acetylcholine receptor. Int Immunopharmacol. 2015 Oct 17. pii: S1567-5769(15)30138-7. doi: 10.1016/j.intimp.2015.10.005. [Epub ahead of print] PubMed PMID: 26490221.

2: Kong FJ, Ma LL, Zhang HH, Zhou JQ. Alpha 7 nicotinic acetylcholine receptor agonist GTS-21 mitigates isoflurane-induced cognitive impairment in aged rats. J Surg Res. 2015 Mar;194(1):255-61. doi: 10.1016/j.jss.2014.09.043. Epub 2014 Oct 5. PubMed PMID: 25450597.

3: Wu S, Zhao H, Luo H, Xiao X, Zhang H, Li T, Zuo X. GTS-21, an α7-nicotinic acetylcholine receptor agonist, modulates Th1 differentiation in CD4(+) T cells from patients with rheumatoid arthritis. Exp Ther Med. 2014 Aug;8(2):557-562. Epub 2014 Jun 3. PubMed PMID: 25009619; PubMed Central PMCID: PMC4079428.

4: Hu Y, Liu R, Li J, Yue Y, Cheng W, Zhang P. Attenuation of Collagen-Induced Arthritis in rat by nicotinic alpha7 receptor partial agonist GTS-21. Biomed Res Int. 2014;2014:325875. doi: 10.1155/2014/325875. Epub 2014 Feb 27. PubMed PMID: 24719855; PubMed Central PMCID: PMC3955649.

5: Sitapara RA, Antoine DJ, Sharma L, Patel VS, Ashby CR Jr, Gorasiya S, Yang H, Zur M, Mantell LL. The α7 nicotinic acetylcholine receptor agonist GTS-21 improves bacterial clearance in mice by restoring hyperoxia-compromised macrophage function. Mol Med. 2014 Jun 19;20:238-47. doi: 10.2119/molmed.2013.00086. PubMed PMID: 24664237; PubMed Central PMCID: PMC4069272.

6: Callahan PM, Terry AV Jr, Tehim A. Effects of the nicotinic α7 receptor partial agonist GTS-21 on NMDA-glutamatergic receptor related deficits in sensorimotor gating and recognition memory in rats. Psychopharmacology (Berl). 2014 Sep;231(18):3695-706. doi: 10.1007/s00213-014-3509-2. Epub 2014 Mar 5. PubMed PMID: 24595504.

7: Thomsen MS, Mikkelsen JD. The α7 nicotinic acetylcholine receptor ligands methyllycaconitine, NS6740 and GTS-21 reduce lipopolysaccharide-induced TNF-α release from microglia. J Neuroimmunol. 2012 Oct 15;251(1-2):65-72. doi: 10.1016/j.jneuroim.2012.07.006. Epub 2012 Aug 9. PubMed PMID: 22884467.

8: Khan MA, Farkhondeh M, Crombie J, Jacobson L, Kaneki M, Martyn JA. Lipopolysaccharide upregulates α7 acetylcholine receptors: stimulation with GTS-21 mitigates growth arrest of macrophages and improves survival in burned mice. Shock. 2012 Aug;38(2):213-9. doi: 10.1097/SHK.0b013e31825d628c. PubMed PMID: 22683726; PubMed Central PMCID: PMC3399057.

9: Cannon CE, Puri V, Vivian JA, Egbertson MS, Eddins D, Uslaner JM. The nicotinic α7 receptor agonist GTS-21 improves cognitive performance in ketamine impaired rhesus monkeys. Neuropharmacology. 2013 Jan;64:191-6. doi: 10.1016/j.neuropharm.2012.05.003. Epub 2012 May 29. PubMed PMID: 22659472.

10: Kox M, Pompe JC, Peters E, Vaneker M, van der Laak JW, van der Hoeven JG, Scheffer GJ, Hoedemaekers CW, Pickkers P. α7 nicotinic acetylcholine receptor agonist GTS-21 attenuates ventilator-induced tumour necrosis factor-α production and lung injury. Br J Anaesth. 2011 Oct;107(4):559-66. doi: 10.1093/bja/aer202. Epub 2011 Jul 18. PubMed PMID: 21771746.

11: Kox M, Pompe JC, Gordinou de Gouberville MC, van der Hoeven JG, Hoedemaekers CW, Pickkers P. Effects of the α7 nicotinic acetylcholine receptor agonist GTS-21 on the innate immune response in humans. Shock. 2011 Jul;36(1):5-11. doi: 10.1097/SHK.0b013e3182168d56. PubMed PMID: 21368716.

12: Chen L, Wang H, Zhang Z, Li Z, He D, Sokabe M, Chen L. DMXB (GTS-21) ameliorates the cognitive deficits in beta amyloid(25-35(-) ) injected mice through preventing the dysfunction of alpha7 nicotinic receptor. J Neurosci Res. 2010 Jun;88(8):1784-94. doi: 10.1002/jnr.22345. PubMed PMID: 20127813.

13: López-Hernández GY, Thinschmidt JS, Morain P, Trocme-Thibierge C, Kem WR, Soti F, Papke RL. Positive modulation of alpha7 nAChR responses in rat hippocampal interneurons to full agonists and the alpha7-selective partial agonists, 4OH-GTS-21 and S 24795. Neuropharmacology. 2009 Mar;56(4):821-30. PubMed PMID: 19705574; PubMed Central PMCID: PMC2775526.

14: Rosas-Ballina M, Goldstein RS, Gallowitsch-Puerta M, Yang L, Valdés-Ferrer SI, Patel NB, Chavan S, Al-Abed Y, Yang H, Tracey KJ. The selective alpha7 agonist GTS-21 attenuates cytokine production in human whole blood and human monocytes activated by ligands for TLR2, TLR3, TLR4, TLR9, and RAGE. Mol Med. 2009 Jul-Aug;15(7-8):195-202. doi: 10.2119/molmed.2009.00039. Epub 2009 Apr 27. PubMed PMID: 19593403; PubMed Central PMCID: PMC2707516.

15: Kox M, van Velzen JF, Pompe JC, Hoedemaekers CW, van der Hoeven JG, Pickkers P. GTS-21 inhibits pro-inflammatory cytokine release independent of the Toll-like receptor stimulated via a transcriptional mechanism involving JAK2 activation. Biochem Pharmacol. 2009 Oct 1;78(7):863-72. doi: 10.1016/j.bcp.2009.06.096. Epub 2009 Jul 1. PubMed PMID: 19576181.

16: Thinschmidt JS, López-Hernández GY, Ren K, King MA, Meyer EM, Papke RL. Modulation of spontaneous hippocampal synaptic events with 5-hydroxyindole, 4OH-GTS-21, and rAAV-mediated alpha7 nicotinic receptor gene transfer. Brain Res. 2008 Apr 8;1203:51-60. doi: 10.1016/j.brainres.2008.02.011. Epub 2008 Feb 14. PubMed PMID: 18321476; PubMed Central PMCID: PMC2577826.

17: Ren K, King MA, Liu J, Siemann J, Altman M, Meyers C, Hughes JA, Meyer EM. The alpha7 nicotinic receptor agonist 4OH-GTS-21 protects axotomized septohippocampal cholinergic neurons in wild type but not amyloid-overexpressing transgenic mice. Neuroscience. 2007 Aug 10;148(1):230-7. Epub 2007 Jul 20. PubMed PMID: 17640819.

18: Kim SW, Ding YS, Alexoff D, Patel V, Logan J, Lin KS, Shea C, Muench L, Xu Y, Carter P, King P, Constanzo JR, Ciaccio JA, Fowler JS. Synthesis and positron emission tomography studies of C-11-labeled isotopomers and metabolites of GTS-21, a partial alpha7 nicotinic cholinergic agonist drug. Nucl Med Biol. 2007 Jul;34(5):541-51. PubMed PMID: 17591554; PubMed Central PMCID: PMC3182824.

19: Pavlov VA, Ochani M, Yang LH, Gallowitsch-Puerta M, Ochani K, Lin X, Levi J, Parrish WR, Rosas-Ballina M, Czura CJ, Larosa GJ, Miller EJ, Tracey KJ, Al-Abed Y. Selective alpha7-nicotinic acetylcholine receptor agonist GTS-21 improves survival in murine endotoxemia and severe sepsis. Crit Care Med. 2007 Apr;35(4):1139-44. PubMed PMID: 17334244.

20: Wei DQ, Sirois S, Du QS, Arias HR, Chou KC. Theoretical studies of Alzheimer's disease drug candidate 3-[(2,4-dimethoxy)benzylidene]-anabaseine (GTS-21) and its derivatives. Biochem Biophys Res Commun. 2005 Dec 16;338(2):1059-64. Epub 2005 Oct 21. PubMed PMID: 16256952.