An Analytical Reference Standard
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28411Bretazenil
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Bretazenil

Item No. 37274

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Synonyms
Synonyms
  • Ro 16-6028
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
Molecular Formula
C19H20BrN3O3
Formula Weight
418.3
Purity
≥98%
Formulation
A crystalline 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
CC(C)(C)OC(C1=C2N(C=N1)C3=CC=CC(Br)=C3C(N4[C@@]2([H])CCC4)=O)=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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    Product Description

    Bretazenil (Item No. 37274) is an analytical reference standard categorized as a GABAA receptor positive allosteric modulator.1 Bretazenil has anxiolytic-like effects in mice.2 It induces self-administration in rhesus monkeys but has a lower physical dependence liability in mice compared with benzodiazepines.3,4 This product is intended for analytical forensic applications. This product is also available as a general research tool (Item No. 28411).

    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. 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).

    3. Licata, S.C., and Rowlett, J.K. Self-administration of bretazenil under progressive-ratio schedules: Behavioral economic analysis of the role intrinsic efficacy plays in the reinforcing effects of benzodiazepines. Drug Alcohol Depend. 113(2-3), 157-164 (2011).

    4. Mirza, N.R., and Nielsen, E.Ø. Do subtype-selective γ-aminobutyric acidA receptor modulators have a reduced propensity to induce physical dependence in mice? J. Pharmacol. Exp. Ther. 316(3), 1378-1385 (2006).