Desmethylflunitrazepam

Desmethylflunitrazepam

Legal status
Legal status	CA: Schedule IV
Identifiers
IUPAC name 5-(2-Fluorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Number	2558-30-7
PubChem (CID)	520217
ChemSpider	453770
UNII	055XLQ0YQ6
ChEMBL	CHEMBL87369
Chemical and physical data
Formula	C15H10FN3O3
Molar mass	299.26 g·mol^−1
3D model (Jmol)	Interactive image
SMILES FC1=C(C=CC=C1)C2=NCC(NC3=C2C=C(C=C3)[N+](=O)[O-])=O
InChI InChI=1S/C15H10FN3O3/c16-12-4-2-1-3-10(12)15-11-7-9(19(21)22)5-6-13(11)18-14(20)8-17-15/h1-7H,8H2,(H,18,20) Key:KNGIGRDYBQPXKQ-UHFFFAOYSA-N

Desmethylflunitrazepam (also known as norflunitrazepam, Ro05-4435 and fonazepam) is a benzodiazepine that is a metabolite of flunitrazepam^[1][2][3] and has been sold online as a designer drug.^[4][5] It has an IC₅₀ value of 1.499 nM for the GABA_A receptor.^[6][7]

See also

• 3-Hydroxyphenazepam
• Adinazolam
• Clonazolam
• Diclazepam
• Etizolam
• Flubromazepam
• Flubromazolam
• Meclonazepam
• Metizolam
• Nifoxipam
• Nitrazolam
• Phenazepam
• Pyrazolam

References

1. Busker, Ruud W.; van Henegouwen, Gerard M. J. Beijersbergen; Kwee, Brigitta M. C.; Winkens, Jos H. M. (May 1987). "Photobinding of flunitrazepam and its major photo-decomposition product N-desmethylflunitrazepam". International Journal of Pharmaceutics. 36 (2–3): 113–120. doi:10.1016/0378-5173(87)90145-1 – via ScienceDirect.
2. Coller, Janet K; Somogyi, Andrew A; Bochner, Felix (20 November 1998). "Quantification of flunitrazepam's oxidative metabolites, 3-hydroxyflunitrazepam and desmethylflunitrazepam, in hepatic microsomal incubations by high-performance liquid chromatography". Journal of Chromatography B: Biomedical Sciences and Applications. 719 (1–2): 87–92. doi:10.1016/S0378-4347(98)00383-1. PMID 9869368 – via ScienceDirect.
3. Kilicarslan, Tansel; Haining, Robert L.; Rettie, Allan E.; Busto, Usanda; Tyndale, Rachel F.; Sellers, Edward M. (1 April 2001). "Flunitrazepam Metabolism by Cytochrome P450s 2C19 and 3A4". Drug Metabolism and Disposition. 29 (4): 460–465. ISSN 1521-009X. PMID 11259331 – via dmd.aspetjournals.org.
4. Moosmann, Bjoern; Bisel, Philippe; Franz, Florian; Huppertz, Laura M.; Auwärter, Volker (2016). "Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines – an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam, and nitrazolam". Journal of Mass Spectrometry. doi:10.1002/jms.3840. ISSN 1096-9888. PMID 27535017 – via Wiley Online Library.
5. Katselou, Maria; Papoutsis, Ioannis; Nikolaou, Panagiota; Spiliopoulou, Chara; Athanaselis, Sotiris (2016). "Metabolites replace the parent drug in the drug arena. The cases of fonazepam and nifoxipam". Forensic Toxicology. doi:10.1007/s11419-016-0338-5. ISSN 1860-8973.
6. Maddalena, Desmond J.; Johnston, Graham A. R. (February 1995). "Prediction of Receptor Properties and Binding Affinity of Ligands to Benzodiazepine/GABA_A Receptors Using Artificial Neural Networks". Journal of Medicinal Chemistry. 38 (4): 715–724. doi:10.1021/jm00004a017. PMID 7861419.
7. So, Sung-Sau; Karplus, Martin (20 December 1996). "Genetic Neural Networks for Quantitative Structure−Activity Relationships: Improvements and Application of Benzodiazepine Affinity for Benzodiazepine/GABA_A Receptors". Journal of Medicinal Chemistry. 39 (26): 5246–5256. doi:10.1021/jm960536o. PMID 8978853.