| Identification | Back Directory | [Name]
imidazenil | [CAS]
151271-08-8 | [Synonyms]
imidazenil
6-(2-Bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide
4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide,6-(2-bromophenyl)-8-fluoro- | [Molecular Formula]
C18H12BrFN4O | [MOL File]
151271-08-8.mol | [Molecular Weight]
399.22 |
| Hazard Information | Back Directory | [Description]
Imidazenil is an imidazobenzodiazepine with the profile of a partial agonist. Animal studies have shown that it does not produce sedation or ataxia in rats nor does it potentiate the effects of alcohol (Guisti et al. 1993). Imidazenil has a low intrinsic activity at the GABAA receptor and therefore causes only slight enhancement of GABA-ergic tone. Its efficacy may, however, be increased when GABA tone is reduced, which could lead to its being active only in conditions where GABA tone is altered. This may well make it an ideal treatment for anxiety and epilepsy. | [Uses]
Imidazenil, a new anxiolytic and anticonvulsant drug, attenuates a benzodiazepine-induced cognition deficit in monkeys. | [Side effects]
When taken by mouth: Ostarine is possibly unsafe. It might cause liver damage and other serious side effects such as heart attack. | [Synthesis]
The synthesis of imidazenil is as follows:
A mixture of 3 g (7.5 mmol) of 6-(2-bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, 300 mL of methylene chloride and 2.25 g (10.8 mmol) of phosphorus pentachloride was stirred at room temperature for 2 hours. Ammonia gas was then introduced until the mixture was basic. After layering with 20 mL of concentrated aqueous ammonia, the mixture was stirred for 15 minutes. The methylene chloride was washed with water, dried and evaporated. The residue was crystallized from ethanol/water to yield 2.4 g of product having the above formula. A second crop of 0.4 g was obtained from the mother liquor for a total yield of 2.8 g. For analysis, a sample of the product was recrystallized from methylene chloride/ethanol and had m.p. 298°-299° C.
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