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definition - Bretazenil

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Bretazenil

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Bretazenil
Systematic (IUPAC) name
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
Identifiers
CAS number84379-13-5
ATC codenone
PubChem107926
ChemSpider97049
Chemical data
FormulaC19H20BrN3O3 
Mol. mass418.284 g/mol
SMILESeMolecules & PubChem
Pharmacokinetic data
Bioavailability ?
Metabolism ?
Half life ?
Excretion ?
Therapeutic considerations
Pregnancy cat. ?
Legal status
Routes ?


Bretazenil (Ro16-6028) is an anxiolytic drug which is derived from the benzodiazepine family, and was invented in 1988. It is most closely related in structure to the benzodiazepine antagonist flumazenil, although its effects are somewhat different.

Bretazenil was originally developed as an anti-anxiety drug, but never commercialised. It is a partial agonist for GABAA receptors in the brain. David Nutt from the University of Bristol has suggested bretazenil as a possible base from which to make a better social drug, as it displays several of the positive effects of alcohol intoxication such as relaxation and sociability, but without the bad effects such as aggression, amnesia, nausea, loss of coordination, liver disease and brain damage. The effects of bretazenil can also be quickly reversed by the action of flumazenil, which is used as an antidote to benzodiazepine overdose,[1] in contrast to alcohol for which there is no effective and reliable antidote.

However, while less addictive than benzodiazepine full agonists such as diazepam[2], long-term use of bretazenil would still be expected to result in dependence and addiction. Bretazenil, were it to be made commercially available, would thus most likely be classed as a controlled substance, e.g. Schedule III or Schedule IV in the USA[citation needed], and so is unlikely to ever be commercialised for recreational use in that country. More liberal jurisdictions however might potentially permit the sale of bretazenil as a recreational alternative to alcohol, especially in countries such as Russia[citation needed] where liver and brain damage from chronic alcohol abuse place a severe burden on the health service[citation needed] and so the potential advantages of a less toxic alternative drug might outweigh the complications of introducing a new recreational drug to the market[citation needed].

Contrary to the results found in animals, no indications for a dissociation of the sedative and anxiolytic effects of bretazenil were found in man. [3] This human study also indicates that Bretazenil is possibly more sedative than Diazepam. The reason is unknown, but the study suggests the possibility that a full-agonist metabolite may be generated in humans but not animals previously tested.

See also

References

  1. ^ Nutt DJ (2006). [Expression error: Missing operand for > "For "Critique and Commentaries" section of the Journal of Psychopharmacology: Alcohol alternatives - a goal for psychopharmacology?"]. Journal of Psychopharmacology 20: 318–320. doi:10.1177/0269881106063042. 
  2. ^ Sellers EM et al. (1992). [Expression error: Missing operand for > "Abuse liability of bretazenil and other partial agonists."]. Clinical Neuropharmacology 15 Suppl 1(Pt A): 409 A. PMID 1354047. 
  3. ^ van Steveninck AL et al. (1996). [Expression error: Missing operand for > "Pharmacokinetic and pharmacodynamic interactions of bretazenil and diazepam with alcohol."]. British Journal of Clinical Pharmacology 41(6): 565–573. PMID 8799523. 


 

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