B6434

Bretazenil

Name: Bretazenil
Brand: SIGMA

≥96% (HPLC), solid

Synonym(e):

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

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Empirische Formel (Hill-System):

C₁₉H₂₀N₃O₃Br

CAS-Nummer:

84379-13-5

Molekulargewicht:

418.28

NACRES:

NA.77

PubChem Substance ID:

329773277

UNSPSC Code:

12352200

MDL number:

MFCD00866987

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Produktname

Bretazenil, ≥96% (HPLC), solid

InChI key

LWUDDYHYYNNIQI-ZDUSSCGKSA-N

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

assay

≥96% (HPLC)

form

solid

color

white

solubility

DMSO: 24 mg/mL
H₂O: insoluble

originator

Roche

storage temp.

2-8°C

Quality Level

100

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Dieser Artikel	L9787	SML0645	SML1438
Sigma-Aldrich B6434 Bretazenil	Sigma-Aldrich L9787 L-655,708	Sigma-Aldrich SML0645 Iomazenil	Sigma-Aldrich SML1438 LY2090314
assay ≥96% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form solid	form powder	form powder	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. -	storage temp. 2-8°C	storage temp. −20°C
solubility DMSO: 24 mg/mL, H₂O: insoluble	solubility DMSO: ≥6.0 mg/mL (Warmed), H₂O: insoluble	solubility DMSO: 5 mg/mL, clear (warmed)	solubility DMSO: 10 mg/mL, clear
color white	color -	color white to beige	color yellow to orange

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).[1] 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.[2]

Biochem/physiol Actions

Bretazenil is a benzodiazepine partial agonist.

Bretazenil is capable of binding to γ-aminobutyric acid type A (GABAA) receptors that are sensitive and insensitive to diazepam.[3] This compound possesses negligible sedative or muscle relaxant effects.[4]

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.

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.[4]

Lagerklasse

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Anxioselective anxiolytics: can less be more?

Anthony S Basile et al.

European journal of pharmacology, 500(1-3), 441-451 (2004-10-07)

Benzodiazepines remain widely used for the treatment of anxiety disorders despite a side-effect profile that includes sedation, myorelaxation, amnesia, and ataxia, and the potential for abuse. gamma-Aminobutyric acid(A) (GABA(A)) receptor partial agonists, subtype-selective agents, and compounds combining both of these

Role of the histidine residue at position 105 in the human alpha 5 containing GABA(A) receptor on the affinity and efficacy of benzodiazepine site ligands.

M D Kelly et al.

British journal of pharmacology, 135(1), 248-256 (2002-01-12)

1. A histidine residue in the N-terminal extracellular region of alpha 1,2,3,5 subunits of the human GABA(A) receptor, which is replaced by an arginine in alpha 4 and alpha 6 subunits, is a major determinant for high affinity binding of

Region-specific and dose-specific effects of chronic haloperidol exposure on [3H]-flumazenil and [3H]-Ro15-4513 GABAA receptor binding sites in the rat brain.

Alba Peris-Yague et al.

European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, 41, 106-117 (2020-11-07)

Postmortem studies suggest that schizophrenia is associated with abnormal expression of specific GABAA receptor (GABAAR) α subunits, including α5GABAAR. Positron emission tomography (PET) measures of GABAAR availability in schizophrenia, however, have not revealed consistent alterations in vivo. Animal studies using

Blockade of behavioral effects of bretazenil by flumazenil and ZK 93,426 in pigeons.

J M Witkin et al.

Pharmacology, biochemistry, and behavior, 56(1), 1-7 (1997-01-01)

Benzodiazepine receptor partial agonists manifest full efficacy in preclinical tests of anxiolytic drug action but do not fully reproduce the discriminative stimulus effects of benzodiazepine receptor full agonists in pigeons. The partial agonist, bretazenil, binds to both diazepam-sensitive and diazepam-insensitive

Mechanism-based pharmacodynamic modeling of the interaction of midazolam, bretazenil, and zolpidem with ethanol.

Bert Tuk et al.

Journal of pharmacokinetics and pharmacodynamics, 29(3), 235-250 (2002-11-27)

The pharmacokinetic and pharmacodynamic interactions of ethanol with the full benzodiazepine agonist midazolam, the partial agonist bretazenil and the benzodiazepine BZ1 receptor subtype selective agonist zolpidem have been determined in the rat in vivo, using an integrated pharmacokinetic-pharmacodynamic approach. Ethanol

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