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Merck
CN

SML0326

Sigma-Aldrich

GTS-21

≥97% (HPLC), α7 Nicotinic Acetylcholine Receptor Agonist, powder

Synonym(s):

3-(2,4-Dimethoxybenzylidene)-anabaseine dihydrochloride, DMBX-anabaseine, DMXB, DMXB-A, GTS21

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About This Item

Empirical Formula (Hill Notation):
C19H20N2O2 · 2HCl
CAS Number:
156223-05-1
Molecular Weight:
381.30
MDL number:
MFCD00941364
UNSPSC Code:
12352200
PubChem Substance ID:
329825331
NACRES:
NA.77

Key Documents

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Product Name

GTS-21, ≥97% (HPLC)

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

faintly yellow to dark yellow

solubility

H2O: >5 mg/mL

storage temp.

2-8°C

SMILES string

Cl.Cl.COc1ccc(\C=C2/CCCN=C2c3cccnc3)c(OC)c1

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+;;

InChI key

BXKYFUGAAFLYJL-BXGYHSFXSA-N

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Application

GTS-21 has been used:
  • as an α7 nicotinic acetylcholine receptors (nAChR) partial agonist to elucidate its anti-inflammatory effects in mouse macrophages
  • to test its protective effect on the renal injury induced by lipopolysaccharide (LPS)
  • to test its effect on microvascular inflammation in endotoxemia induced by LPS

Biochem/physiol Actions

GTS-2, a derivative of anisine is an immunomodulatory drug. It is used for treating pancreatitis and septicemia. GTS-2 inhibits the pro-inflammatory cytokines especially the interleukin-6 (IL6) and tumor necrosis factor (TNF) in sepsis and endotoxemia.
GTS-21 is a selective agonist at α-7 nicotinic receptors with anti-inflammatory and cognition enhancing activities. GTS-21 has also been investigated for the treatment of schizophrenia.
GTS-21 is a selective agonist at α-7 nicotinic receptors.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000481457
0000481456
0000390173
0000390173
0000238719

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M Kox et al.
British journal of anaesthesia, 107(4), 559-566 (2011-07-21)
Mechanical ventilation (MV) induces an inflammatory response that can lead to lung injury. The vagus nerve can limit the inflammatory response through the cholinergic anti-inflammatory pathway. We evaluated the effects of stimulation of the cholinergic anti-inflammatory pathway with the selective
Christopher E Cannon et al.
Neuropharmacology, 64, 191-196 (2012-06-05)
The cognitive deficits associated with schizophrenia are recognized as a core component of the disorder, yet there remain no available therapeutics to treat these symptoms of the disease. As a result, there is a need for establishing predictive preclinical models
Mauricio Rosas-Ballina et al.
Molecular medicine (Cambridge, Mass.), 15(7-8), 195-202 (2009-07-14)
The cholinergic antiinflammatory pathway modulates inflammatory cytokine production through a mechanism dependent on the vagus nerve and the alpha7 subunit of the nicotinic acetylcholine receptor. GTS-21 [3-(2,4-dimethoxybenzylidene) anabaseine], a selective alpha7 agonist, inhibits inflammatory cytokine production in murine and human
Peng Sun et al.
Shock (Augusta, Ga.), 49(6), 698-703 (2017-08-12)
Studies have demonstrated that vagus nerve stimulation (VNS) reduces ischemia/reperfusion injury. In this study, we investigated the protective effects of VNS in a rat model of cardiopulmonary resuscitation (CPR). We further investigated whether the beneficial effects of VNS were dependent
Jerry J Buccafusco et al.
Biochemical pharmacology, 78(7), 852-862 (2009-07-07)
In monkeys proficient in the performance of a computer-assisted delayed response task, administration of sub-sedative doses of ketamine significantly impaired task performance after the 2mg/kg dose, producing a decrease in accuracies across all four delay intervals. Ketamine elicited occasional and
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