GTS-21 HCl, ≥98%

GTS-21 HCl ≥98%

Chemical Name:      3-(2,4-Dimethoxybenzylidene)-anabaseine dihydrochloride
Synonyms:     3-(2,4-Dimethoxybenzylidene)-anabaseine dihydrochloride, DMBX-anabaseine, DMXB-A, GTS21, 3-(2,4-dimethoxybenzylidene)-3,4,5,6-tetrahydro-2,3'-bipyridine dihydrochloride

CAS Number:    156223-05-1

GTS-21 is a selective agonist at α7 nicotinic receptors with anti-inflammatory and cognition enhancing properties.

Form:    Bright yellow to deep yellow powder
Molecular Formula:    C19H20N2O2 · 2HCl

Molecular Weight:    381.30 g/mol
Melting Point:    216-217°C (decomp)



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Chemical Information

CAS Number:156223-05-1
Purity:≥98%
Molecular Weight:381.30 g/mol
Melting Point:216-217°C (decomp)
Molecular Formula:C19H20N2O2 · 2HCl
Synonyms:3-(2,4-Dimethoxybenzylidene)-anabaseine dihydrochloride, DMBX-anabaseine, DMXB-A, GTS21, 3-(2,4-dimethoxybenzylidene)-3,4,5,6-tetrahydro-2,3'-bipyridine dihydrochloride
PubChem CID:329825331
SMILES:C1C(/C=C(\CC2)C(=NC2)C(C=NC2)=CC=2)=C(C=C(C=1)OC)OC

Technical Information

Application:GTS-21 is a selective agonist at α7 nicotinic receptors with anti-inflammatory and cognition enhancing properties.
Appearance:Bright yellow to deep yellow powder
Physical State:Solid
Solubility:Soluble in Ethanol, Soluble in Water.
Storage:Store at room temperature or cooler, in a sealed airtight container, protected from heat, light and humidity.
Stability:Stable for at least two years when stored as above.

Scientific research:

GTS-21 (DMBX-A) is a derivative of anabaseine that acts as a selective partial agonist at α7 nicotinic acetylcholine receptors.[1][2]

GTS-21 and its demethylated active metabolite 4-OH-GTS-21[3] display nootropic[4] and neuroprotective effects,[5][6][7][8] and GTS-21 has been investigated for the treatment of Alzheimer's disease,[9] nicotine dependence,[10] and schizophrenia.[10][11][12][13][14][15]

References

  • [1] Briggs CA, Anderson DJ, Brioni JD, Buccafusco JJ, Buckley MJ, Campbell JE, Decker MW, Donnelly-Roberts D, Elliott RL, Gopalakrishnan M, Holladay MW, Hui YH, Jackson WJ, Kim DJ, Marsh KC, O'Neill A, Prendergast MA, Ryther KB, Sullivan JP, Arneric SP. Functional characterization of the novel neuronal nicotinic acetylcholine receptor ligand GTS-21 in vitro and in vivo. Pharmacology, Biochemistry and Behaviour. 1997 May-Jun;57(1-2):231-41. PMID 9164577
  • [2] Meyer EM, Tay ET, Papke RL, Meyers C, Huang GL, de Fiebre CM. 3-[2,4-Dimethoxybenzylidene]anabaseine (DMXB) selectively activates rat alpha7 receptors and improves memory-related behaviors in a mecamylamine-sensitive manner. Brain Research. 1997 Sep 12;768(1-2):49-56. PMID 9369300
  • [3] Meyer EM, Kuryatov A, Gerzanich V, Lindstrom J, Papke RL. Analysis of 3-(4-hydroxy, 2-Methoxybenzylidene)anabaseine selectivity and activity at human and rat alpha-7 nicotinic receptors. Journal of Pharmacology and Experimental Therapeutics. 1998 Dec;287(3):918-25. PMID 9864273
  • [4] Kitagawa H, Takenouchi T, Azuma R, Wesnes KA, Kramer WG, Clody DE, Burnett AL. Safety, pharmacokinetics, and effects on cognitive function of multiple doses of GTS-21 in healthy, male volunteers. Neuropsychopharmacology. 2003 Mar;28(3):542-51. PMID 12629535
  • [5] Meyer EM, King MA, Meyers C. Neuroprotective effects of 2,4-dimethoxybenzylidene anabaseine (DMXB) and tetrahydroaminoacridine (THA) in neocortices of nucleus basalis lesioned rats. Brain Research. 1998 Mar 9;786(1-2):252-4. PMID 9555043
  • [6] Shimohama S, Greenwald DL, Shafron DH, Akaika A, Maeda T, Kaneko S, Kimura J, Simpkins CE, Day AL, Meyer EM. Nicotinic alpha 7 receptors protect against glutamate neurotoxicity and neuronal ischemic damage. Brain Research. 1998 Jan 1;779(1-2):359-63. PMID 9473725
  • [7] Li Y, Meyer EM, Walker DW, Millard WJ, He YJ, King MA. Alpha7 nicotinic receptor activation inhibits ethanol-induced mitochondrial dysfunction, cytochrome c release and neurotoxicity in primary rat hippocampal neuronal cultures. Journal of Neurochemistry. 2002 May;81(4):853-8. PMID 12065644
  • [8] de Fiebre NC, de Fiebre CM. Alpha 7 nicotinic acetylcholine receptor-mediated protection against ethanol-induced neurotoxicity. Alcohol. 2003 Nov;31(3):149-53. PMID 14693263
  • [9] Kem WR. The brain alpha7 nicotinic receptor may be an important therapeutic target for the treatment of Alzheimer's disease: studies with DMXBA (GTS-21). Behavioural Brain Research. 2000 Aug;113(1-2):169-81. PMID 10942043
  • [10] Foulds J, Burke M, Steinberg M, Williams JM, Ziedonis DM. Advances in pharmacotherapy for tobacco dependence. Expert Opinion on Emerging Drugs. 2004 May;9(1):39-53. PMID 15155135
  • [11] Simosky JK, Stevens KE, Freedman R. Nicotinic agonists and psychosis. Current Drug Targets. CNS and Neurological Disorders. 2002 Apr;1(2):149-62. PMID 12769624
  • [12] Martin LF, Kem WR, Freedman R. Alpha-7 nicotinic receptor agonists: potential new candidates for the treatment of schizophrenia. Psychopharmacology. 2004 Jun;174(1):54-64. PMID 15205879
  • [13] Olincy A, Harris JG, Johnson LL, Pender V, Kongs S, Allensworth D, Ellis J, Zerbe GO, Leonard S, Stevens KE, Stevens JO, Martin L, Adler LE, Soti F, Kem WR, Freedman R. Proof-of-concept trial of an alpha7 nicotinic agonist in schizophrenia. Archives of General Psychiatry. 2006 Jun;63(6):630-8. PMID 16754836
  • [14] Olincy A, Stevens KE. Treating schizophrenia symptoms with an alpha7 nicotinic agonist, from mice to men. Biochemical Pharmacology. 2007 Oct 15;74(8):1192-201. PMID 17714692
  • [15] Freedman R, Olincy A, Buchanan RW, Harris JG, Gold JM, Johnson L, Allensworth D, Guzman-Bonilla A, Clement B, Ball MP, Kutnick J, Pender V, Martin LF, Stevens KE, Wagner BD, Zerbe GO, Soti F, Kem WR. Initial Phase 2 Trial of a Nicotinic Agonist in Schizophrenia. American Journal of Psychiatry. 2008 Apr 1. PMID 18381905

Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.