B6434
Bretazenil
≥96% (HPLC), solid
Synonym(s):
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
Empirical Formula (Hill Notation):
C19H20N3O3Br
CAS Number:
Molecular Weight:
418.28
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
Elisabetta Cagetti et al.
Molecular pharmacology, 63(1), 53-64 (2002-12-19)
One of the pharmacological targets of ethanol is the GABAA receptor (GABAR), whose function and expression are altered after chronic administration of ethanol. The details of the changes differ between experimental models. In the chronic intermittent ethanol (CIE) model for
M Nazar et al.
Journal of neural transmission (Vienna, Austria : 1996), 106(5-6), 369-381 (1999-08-12)
The effects of an intrahippocampal administering of a nonselective full (midazolam), a partial benzodiazepine (BDZ) receptor agonist (bretazenil), and a BDZ1 selective (zolpidem) receptor ligand were examined in the open field test (OFT) of neophobia and Vogel's test (VT) of
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