Bretazenil

Base Information

• Chemical Name: Bretazenil
• CAS No.: 84379-13-5
• Molecular Formula: C19H20BrN3O3
• Molecular Weight: 418.29
• UNII: OSZ0E9DGOJ
• DSSTox Substance ID: DTXSID6046266
• Nikkaji Number: J246.968E
• Wikipedia: Bretazenil
• Wikidata: Q4961977
• NCI Thesaurus Code: C72111
• ChEMBL ID: CHEMBL366947
• Mol file: 84379-13-5.mol

Synonyms:bretazenil;Ro 16-6028;Ro-16-6028;t-butyl-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)-pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylate

Chemical Property of Bretazenil

Chemical Property:

• Vapor Pressure: 4.29E-14mmHg at 25°C
• Refractive Index: 1.685
• Boiling Point: 594.3 °C at 760 mmHg
• PKA: 0.78±0.20(Predicted)
• Flash Point: 313.2 °C
• PSA: 64.43000
• Density: 1.56 g/cm³
• LogP: 3.81870
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 24 mg/mL, soluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 417.06880
• Heavy Atom Count: 26
• Complexity: 593

Purity/Quality:

99% ^*data from raw suppliers

Bretazenil ≥96% (HPLC), solid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1=C2C3CCCN3C(=O)C4=C(N2C=N1)C=CC=C4Br
• Isomeric SMILES: CC(C)(C)OC(=O)C1=C2[C@@H]3CCCN3C(=O)C4=C(N2C=N1)C=CC=C4Br
• Description: Bretazenil is an imidazobenzodiazepine partial agonist and a potent anxiolytic. It is rapidly absorbed and has a half-life of 2.5 hours. Animal work has shown that, even after long-term administration of bretazenil, there are no changes in GABA receptor binding or function, and tolerance does not occur. Studies in humans have also suggested that bretazenil has a low abuse potential (Sellers et al. 1991). In terms of clinical effects, bretazenil has demonstrated anxiolytic efficacy in both generalized anxiety disorder and panic disorder (Katschnig et al. 1991), but no controlled study has compared bretazenil with a classic full agonist.
• Uses: Anti-anxiety agent.Bretazenil potentiated GABA responses on α4β3γ2 cells.Bretazenil is a partial benzodiazepine receptor agonist. Benzodiazepines, mainly diazepam, are commonly used as anticonvulsants in the treatment of organophosphate casualties. 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.

Technology Process of Bretazenil

There total 3 articles about Bretazenil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(11aS)-6-bromo-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione (90450-72-9) → bretazenil (84379-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide

2: tBuOK / dimethylformamide

With potassium tert-butylate; sodium hydride; In N,N-dimethyl-formamide; 1: Substitution / 2: cyclocondensation;

DOI:10.1071/CH99135

Reference yield:

tert-Butyl isocyanoacetate (2769-72-4) + phosphoric acid 6-bromo-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-11-yl ester diethyl ester → bretazenil (84379-13-5)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide;

DOI:10.1071/CH99135

Reference yield:

tert-Butyl isocyanoacetate (2769-72-4) + (11aS)-6-bromo-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione (90450-72-9) → bretazenil (84379-13-5)

Guidance literature:

With sodium hydride; diethyl chlorophosphate; Yield given. Multistep reaction;

DOI:10.1002/(SICI)1099-1344(199609)38:9<835::AID-JLCR898>3.0.CO;2-Z

upstream raw materials:

tert-Butyl isocyanoacetate

(11aS)-6-bromo-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Refernces

• 1、 Katsifis, Andrew,Mattner, Filomena,McPhee, Meredith,Kassiou, Michael,Najdovski, Ljubco,Dikic, Branko. "Synthesis of iodine-123 labelled analogues of the partial agonist (S)- and (R)-bretazenil for the study of CNS benzodiazepine receptors using SPECT". . p. 835 - 845. Retrieved 2007/10/03.