Desmethylflunitrazepam

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 GABAA receptor.[6][7]

Desmethylflunitrazepam
Legal status
Legal status
Identifiers
IUPAC name
  • 5-(2-Fluorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.018.072
Chemical and physical data
FormulaC15H10FN3O3
Molar mass299.261 g·mol−1
3D model (JSmol)
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

See also

References
  1. Busker RW, van Henegouwen GM, Kwee BM, Winkens JH (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.
  2. Coller JK, Somogyi AA, Bochner F (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.
  3. Kilicarslan T, Haining RL, Rettie AE, Busto U, Tyndale RF, Sellers EM (April 2001). "Flunitrazepam metabolism by cytochrome P450S 2C19 and 3A4". Drug Metabolism and Disposition. 29 (4 Pt 1): 460–5. PMID 11259331.
  4. Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V (November 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. 51 (11): 1080–1089. Bibcode:2016JMSp...51.1080M. doi:10.1002/jms.3840. PMID 27535017.
  5. Katselou M, Papoutsis I, Nikolaou P, Spiliopoulou C, Athanaselis S (2016). "Metabolites replace the parent drug in the drug arena. The cases of fonazepam and nifoxipam". Forensic Toxicology. 35 (1): 1–10. doi:10.1007/s11419-016-0338-5. PMC 5214877. PMID 28127407.
  6. Maddalena DJ, Johnston GA (February 1995). "Prediction of receptor properties and binding affinity of ligands to benzodiazepine/GABAA receptors using artificial neural networks". Journal of Medicinal Chemistry. 38 (4): 715–24. doi:10.1021/jm00004a017. PMID 7861419.
  7. So SS, Karplus M (December 1996). "Genetic neural networks for quantitative structure-activity relationships: improvements and application of benzodiazepine affinity for benzodiazepine/GABAA receptors". Journal of Medicinal Chemistry. 39 (26): 5246–56. doi:10.1021/jm960536o. PMID 8978853.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.