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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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Prodyot K Chatterjee et al.
PloS one, 7(5), e35361-e35361 (2012-05-16)
Sepsis is one of the leading causes of acute kidney injury (AKI). Septic patients who develop acute kidney injury (AKI) are at increased risk of death. To date there is no effective treatment for AKI or septic AKI. Based on
Jason R Tregellas et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 35(4), 938-942 (2009-12-04)
3-(2,4-Dimethoxybenzylidene)-anabaseine (DMXB-A) is a partial agonist at alpha7-nicotinic acetylcholine receptors and is now in early clinical development for treatment of deficits in neurocognition and sensory gating in schizophrenia. During its initial phase 2 test, functional magnetic resonance imaging (fMRI) studies
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
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
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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