IUPAC/Chemical Name
4H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxamide, 6-(2-bromophenyl)-8-fluoro-
InChi Key
OCJHYHKWUWSHEN-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H12BrFN4O/c19-13-4-2-1-3-11(13)16-12-7-10(20)5-6-14(12)24-9-23-17(18(21)25)15(24)8-22-16/h1-7,9H,8H2,(H2,21,25)
SMILES Code
NC(=O)c1ncn2c1CN=C(c3ccccc3Br)c4cc(F)ccc24
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Imidazenil is a partial positive allosteric modulator of gamma-aminobutyric acid action at GABA(A) receptors.
In vivo activity:
Using patas monkeys and a multiple schedule with repeated acquisition and performance of chain responses, this study reports that IMD (imidazenil) administration for 17 days antagonized without showing tolerance ALP-induced disruption of acquisition.
Reference: Proc Natl Acad Sci U S A. 2000 Feb 29;97(5):2314-9. https://pubmed.ncbi.nlm.nih.gov/10696114/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
399.22
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Auta J, Guidotti A, Costa E. Imidazenil prevention of alprazolam-induced acquisition deficit in patas monkeys is devoid of tolerance. Proc Natl Acad Sci U S A. 2000 Feb 29;97(5):2314-9. doi: 10.1073/pnas.97.5.2314. PMID: 10696114; PMCID: PMC15798.
2. Pibiri F, Kozikowski AP, Pinna G, Auta J, Kadriu B, Costa E, Guidotti A. The combination of huperzine A and imidazenil is an effective strategy to prevent diisopropyl fluorophosphate toxicity in mice. Proc Natl Acad Sci U S A. 2008 Sep 16;105(37):14169-74. doi: 10.1073/pnas.0807172105. Epub 2008 Sep 10. PMID: 18784370; PMCID: PMC2544596.
In vivo protocol:
1. Auta J, Guidotti A, Costa E. Imidazenil prevention of alprazolam-induced acquisition deficit in patas monkeys is devoid of tolerance. Proc Natl Acad Sci U S A. 2000 Feb 29;97(5):2314-9. doi: 10.1073/pnas.97.5.2314. PMID: 10696114; PMCID: PMC15798.
2. Pibiri F, Kozikowski AP, Pinna G, Auta J, Kadriu B, Costa E, Guidotti A. The combination of huperzine A and imidazenil is an effective strategy to prevent diisopropyl fluorophosphate toxicity in mice. Proc Natl Acad Sci U S A. 2008 Sep 16;105(37):14169-74. doi: 10.1073/pnas.0807172105. Epub 2008 Sep 10. PMID: 18784370; PMCID: PMC2544596.
1. Kadriu B, Guidotti A, Costa E, Auta J. Imidazenil, a non-sedating anticonvulsant benzodiazepine, is more potent than diazepam in protecting against DFP-induced seizures and neuronal damage. Toxicology. 2009 Feb 27;256(3):164-74. doi: 10.1016/j.tox.2008.11.021. Epub 2008 Dec 7. PMID: 19111886.
2. Auta J, Giusti P, Guidotti A, Costa E. Imidazenil, a partial positive allosteric modulator of GABAA receptors, exhibits low tolerance and dependence liabilities in the rat. J Pharmacol Exp Ther. 1994 Sep;270(3):1262-9. PMID: 7932179.
3. Auta J, Costa E, Davis J, Guidotti A. Imidazenil: a potent and safe protective agent against diisopropyl fluorophosphate toxicity. Neuropharmacology. 2004 Mar;46(3):397-403. doi: 10.1016/j.neuropharm.2003.09.010. PMID: 14975695.
4. Giusti P, Ducić I, Puia G, Arban R, Walser A, Guidotti A, Costa E. Imidazenil: a new partial positive allosteric modulator of gamma-aminobutyric acid (GABA) action at GABAA receptors. J Pharmacol Exp Ther. 1993 Aug;266(2):1018-28. PMID: 8394902.
