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Merck

B6434

Sigma-Aldrich

Bretazenil

≥96% (HPLC), solid

Sinónimos:

9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid, Ro 16-6028

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About This Item

Fórmula empírica (notación de Hill):
C19H20N3O3Br
Número de CAS:
Peso molecular:
418.28
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥96% (HPLC)

form

solid

color

white

solubility

DMSO: 24 mg/mL
H2O: insoluble

originator

Roche

storage temp.

2-8°C

SMILES string

[H][C@@]12CCCN1C(=O)c3c(Br)cccc3-n4cnc(C(=O)OC(C)(C)C)c24

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

General description

Bretazenil, a tetracyclic imidazocarboxylic ester, is an anxi-olytic/anticonvulsant agent. It possesses a half-life of 2.5 hours and is quickly absorbed.

Application

Bretazenil has been used to determine non-specific binding due to its affinity to bind to a variety of γ-aminobutyric acid type A (GABAA) receptor subtypes (α1-3;5). It has also been used as a GABAA receptor partial agonist in the subcutaneous Alzet minipumps to treat obese agouti?related protein (AgRP)?ablated and lean naive mice to study its effect on them.

Biochem/physiol Actions

Bretazenil is capable of binding to γ-aminobutyric acid type A (GABAA) receptors that are sensitive and insensitive to diazepam. This compound possesses negligible sedative or muscle relaxant effects.
Bretazenil is a benzodiazepine partial agonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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Visite la Librería de documentos

L Mathiasen et al.
Psychopharmacology, 182(4), 475-484 (2005-09-01)
GABAA receptors containing an alpha2 subunit are proposed to mediate the anxiolytic effect of benzodiazepines (BZ) based on studies in transgenic mice using unconditioned models of anxiety. Conditioned models of anxiety were not assessed and are rarely encountered in phenotyping
Aurélie Joly-Amado et al.
The EMBO journal, 31(22), 4276-4288 (2012-09-20)
Obesity-related diseases such as diabetes and dyslipidemia result from metabolic alterations including the defective conversion, storage and utilization of nutrients, but the central mechanisms that regulate this process of nutrient partitioning remain elusive. As positive regulators of feeding behaviour, agouti-related
G Munro et al.
The Journal of pharmacology and experimental therapeutics, 327(3), 969-981 (2008-09-16)
Spinal administration of GABA(A) receptor modulators, such as the benzodiazepine drug diazepam, partially alleviates neuropathic hypersensitivity that manifests as spontaneous pain, allodynia, and hyperalgesia. However, benzodiazepines are hindered by sedative impairments and other side effect issues occurring mainly as a
M R Guscott et al.
Behavioural pharmacology, 11(6), 495-504 (2000-12-05)
In the rat, fear-potentiated startle (FPS) test animals are first trained to associate brief light presentations with a mild electric footshock and then tested for startle responses to acoustic stimuli, delivered either in darkness (i.e. baseline startle) or after the
N Brown et al.
British journal of pharmacology, 136(7), 965-974 (2002-07-30)
1: The pharmacology of the stable cell line expressing human alpha(4)beta(3)delta GABA(A) receptor was investigated using whole-cell patch-clamp techniques. 2: alpha(4)beta(3)delta receptors exhibited increased sensitivity to GABA when compared to alpha(4)beta(3)gamma(2) receptors, with EC(50)'s of 0.50 (0.46, 0.53) microM and

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