A positive allosteric modulator of GABAA receptors
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Analytical Standard(s)
37274Bretazenil
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Bretazenil

Item No. 28411

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-bromo-11,12,13,13aS-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid, 1,1-dimethylethyl ester
CAS Number
84379-13-5
Synonyms
  • Ro 16-6028
Molecular Formula
C19H20BrN3O3
Formula Weight
418.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): Partially soluble
λmax
217 nm
SMILES
BrC1=CC=CC(N2C([C@@]3([H])N4CCC3)=C(C(OC(C)(C)C)=O)N=C2)=C1C4=O
InChi Code
InChI=1S/C19H20BrN3O3/c1-19(2,3)26-18(25)15-16-13-8-5-9-22(13)17(24)14-11(20)6-4-7-12(14)23(16)10-21-15/h4,6-7,10,13H,5,8-9H2,1-3H3/t13-/m0/s1
InChi Key
LWUDDYHYYNNIQI-ZDUSSCGKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    Bretazenil is a positive allosteric modulator of GABAA receptors with anticonvulsant and anxiolytic activity.1 It potentiates GABA-gated chloride currents in rat cortical neurons and in HEK293 cells expressing α1β1γ2 subunit-containing GABAA receptors (EC50s = 60 and 10 nM, respectively).1 Bretazenil inhibits binding of the benzodiazepine diazepam to rat cerebral cortex homogenates (IC50 = 2.2 nM).2 It inhibits tonic convulsions induced by pentylenetetrazol (PTZ; Item No. 18682) and maximal electroshock (MES) in rats (ED50s = 0.07 and 0.48 mg/kg, respectively). Bretazenil (5-30 mg/kg) increases the number of open arm entries and percentage of time spent in the open arms of the elevated plus maze in mice, indicating anxiolytic-like activity.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Puia, G., Dučič, I., Vicini, S., et al. Molecular mechanisms of the partial allosteric modulatory effects of bretazenil at γ-aminobutyric acid type A receptor. Proc. Natl. Acad. Sci. USA 89(8), 3620-3624 (1992).

    2. Martin, J.R., Pieri, L., Bonetti, E.P., et al. Ro 16-6028: A novel anxiolytic acting as a partial agonist at the benzodiazepine receptor. Pharmacopsychiatry 21(6), 360-362 (1988).

    3. Cole, J.C., and Rodgers, R.J. An ethological analysis of the effects of chlordiazepoxide and bretazenil (Ro 16-6028) in the murine elevated plus-maze. Behav. Pharmacol. 4(6), 573-580 (1993).