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SML0326

Sigma-Aldrich

GTS-21

≥97% (HPLC)

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

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

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bianca Brawek et al.
International journal of molecular sciences, 22(3) (2021-01-28)
Microglia, the innate immune cells of the brain, are commonly perceived as resident macrophages of the central nervous system (CNS). This definition, however, requires further specification, as under healthy homeostatic conditions, neither morphological nor functional properties of microglia mirror those
Ryan E Hibbs et al.
The EMBO journal, 28(19), 3040-3051 (2009-08-22)
The pentameric acetylcholine-binding protein (AChBP) is a soluble surrogate of the ligand binding domain of nicotinic acetylcholine receptors. Agonists bind within a nest of aromatic side chains contributed by loops C and F on opposing faces of each subunit interface.
Caijuan Shi et al.
Journal of molecular modeling, 19(2), 871-878 (2012-10-23)
Nicotinic acetylcholine receptors (nAChRs) are drug targets for neuronal disorders and diseases. Partial agonists for nAChRs are currently being developed as drugs for the treatment of neurological diseases for their relative safety originated from reduced excessive stimulation. In the current
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
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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