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SML2447

Sigma-Aldrich

TPA023

≥98% (HPLC)

Synonym(s):

7-(1,1-Dimethylethyl)-6-[(1-ethyl-1H-1,2,4-triazol-5-yl)methoxy]-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine, TPA 023

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About This Item

Empirical Formula (Hill Notation):
C20H22FN7O
CAS Number:
252977-51-8
Molecular Weight:
395.43
MDL number:
MFCD29921350
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

CC(C)(C)C1=CC2=NN=C(C3=CC=CC=C3F)N2N=C1OCC4=NC=NN4CC

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

InChI key

QKIWQBLNTSQOLY-UHFFFAOYSA-N

Biochem/physiol Actions

Highly potent alpha2/alph3 GABA-A receptor partial agonist for benzodiazepine binding site with anxiolytic activity but lacking sedative activity
TPA023 is a highly potent, functionally selective agonist for α2-, α3-, and α5GABAA receptors that shows zero efficacy at a1GABAA subtypes. TPA023 exhibits anxiolytic and anticonvulsant effects in both animals and humans but lacks sedative effects and abuse potential.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000067033
0000067032
0000061412

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Nina M Shinday et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 38(6), 1006-1014 (2013-01-11)
Benzodiazepines are prescribed widely but their utility is limited by unwanted side effects, including abuse potential. The mechanisms underlying the abuse-related effects of benzodiazepines are not well understood, although α1 subunit-containing GABAA receptors have been proposed to have a critical
John R Atack et al.
The Journal of pharmacology and experimental therapeutics, 332(1), 17-25 (2009-09-26)
The GABA(A) receptor alpha2/alpha3 subtype-selective compound 7-(1,1-dimethylethyl)-6-(2-ethyl-2H-1,2,4-triazol-3-ylmethoxy)-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine (TPA023; also known as MK-0777) is a triazolopyridazine that has similar, subnanomolar affinity for the benzodiazepine binding site of alpha1-, alpha2-, alpha3-, and alpha5-containing GABA(A) receptors and has partial agonist efficacy at the
Angela N Duke et al.
The Journal of pharmacology and experimental therapeutics, 366(1), 145-157 (2018-05-04)
In nonhuman primates we tested a new set of behavioral categories for observable sedative effects using pediatric anesthesiology classifications as a basis. Using quantitative behavioral observation techniques in rhesus monkeys, we examined the effects of alprazolam and diazepam (nonselective benzodiazepines)

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