ChemicalBook > CAS DataBase List > 7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product Name
7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine
CAS No.
252977-51-8
Chemical Name
7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine
Synonyms
TPA 023;TPA 023, 10 mM in DMSO;7-tert-butyl-6-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine;7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine;inhibit,γ-Aminobutyric acid Receptor,TPA 023,Inhibitor,Gamma-aminobutyric acid Receptor,TPA-023,GABA Receptor,TPA023;1,2,4-Triazolo[4,3-b]pyridazine, 7-(1,1-dimethylethyl)-6-[(1-ethyl-1H-1,2,4-triazol-5-yl)methoxy]-3-(2-fluorophenyl)-
CBNumber
CB83164844
Molecular Formula
C20H22FN7O
Formula Weight
395.43
MOL File
252977-51-8.mol
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7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine Property

Density 
1.33±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Soluble in DMSO
pka
2.08±0.10(Predicted)
form 
Solid
color 
White to off-white
InChI
1S/C20H22FN7O/c1-5-27-17(22-12-23-27)11-29-19-14(20(2,3)4)10-16-24-25-18(28(16)26-19)13-8-6-7-9-15(13)21/h6-10,12H,5,11H2,1-4H3
InChIKey
QKIWQBLNTSQOLY-UHFFFAOYSA-N
SMILES
CC(C)(C)C1=CC2=NN=C(C3=CC=CC=C3F)N2N=C1OCC4=NC=NN4CC
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Safety

WGK Germany 
WGK 3
Storage Class
11 - Combustible Solids
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML2447
Product name
TPA023
Purity
≥98% (HPLC)
Packaging
5MG
Price
$86
Updated
2025/07/31
Sigma-Aldrich
Product number
SML2447
Product name
TPA023
Purity
≥98% (HPLC)
Packaging
25MG
Price
$325
Updated
2025/07/31
ChemScene
Product number
CS-6795
Product name
TPA023
Purity
99.71%
Packaging
1mg
Price
$450
Updated
2021/12/16
ChemScene
Product number
CS-6795
Product name
TPA023
Purity
99.71%
Packaging
5mg
Price
$950
Updated
2021/12/16
ChemScene
Product number
CS-6795
Product name
TPA023
Purity
99.71%
Packaging
10mg
Price
$1600
Updated
2021/12/16
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7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical Properties,Usage,Production

Uses

TPA 023 is a GABAA α2/α3 subtype-selective agonist, with Ki of 0.19-0.41 nM.

Biological Activity

TPA023 is a highly potent, functionally selective agonist for α2-, α3-, and α5GABAA receptors th at shows zero efficacy at a1GABAA subtypes. TPA023 exhibits anxiolytic and anticonvulsant effects in both animals and humans but lacks sedative effects and abuse potential.

in vivo

TPA023 displays good receptor occupancy, when administered orally to rats. The dose of TPA023 resulting in 50% occupancy of rat brain GABAA receptors is 0.42 mg/kg, with the corresponding plasma concentration being 25 ng/mL. TPA023 is also efficacious in the mouse pentylenetetrazole-induced seizure model, providing full seizure protection at a dose of 10 mg/kg i.p. (84% occupancy), with the ED50 of 0.19-0.41 nM, for protection against tonic convulsions (1.4 mg/kg i.p.) corresponding to around 50% occupancy. TPA023 (3 mg/kg p.o. in 0.5% methyl cellulose) shows anxiolytic-like effect on rats[1]. TPA023 (0.7, 2.0, and 5 mg/kg, p.o.) blocks ketamine's cognitive-impairing ability but does not influence the behavioral symptoms of rhesus monkeys[2].

References

[1] Atack JR. Subtype-selective GABA(A) receptor modulation yields a novel pharmacological profile: the design and development of TPA023. Adv Pharmacol. 2009;57:137-85 DOI:10.1016/S1054-3589(08)57004-9
[2] Castner SA, et al. Reversal of ketamine-induced working memory impairments by the GABAAalpha2/3 agonist TPA023. Biol Psychiatry. 2010 May 15;67(10):998-1001. DOI:10.1016/j.biopsych.2010.01.001

7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine Preparation Products And Raw materials

Raw materials

Preparation Products

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7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine Suppliers

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252977-51-8, 7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineRelated Search:


  • TPA 023
  • 7-tert-butyl-6-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine
  • 7-(tert-butyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine
  • 1,2,4-Triazolo[4,3-b]pyridazine, 7-(1,1-dimethylethyl)-6-[(1-ethyl-1H-1,2,4-triazol-5-yl)methoxy]-3-(2-fluorophenyl)-
  • inhibit,γ-Aminobutyric acid Receptor,TPA 023,Inhibitor,Gamma-aminobutyric acid Receptor,TPA-023,GABA Receptor,TPA023
  • TPA 023, 10 mM in DMSO
  • 252977-51-8
  • C20H22FN7O