desmethylflunitrazepam

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 5-(2-Fluorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one

| image = Desmethylflunitrazepam.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_CA = Schedule IV

| legal_DE = NpSG

| legal_UK = PSA

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 2558-30-7

| ATC_prefix =

| ATC_suffix =

| PubChem = 520217

| ChemSpiderID = 453770

| ChEMBL = 87369

| UNII = 055XLQ0YQ6

| C=15 | H=10 | F=1 | N=3 | O=3

| molecular_weight =

| melting_point =

| smiles = FC1=C(C=CC=C1)C2=NCC(NC3=C2C=C(C=C3)[N+](=O)[O-])=O

| StdInChI = 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)

| StdInChIKey = KNGIGRDYBQPXKQ-UHFFFAOYSA-N

}}

Desmethylflunitrazepam (also known as norflunitrazepam, Ro05-4435 and fonazepam) is a benzodiazepine that is a metabolite of flunitrazepam{{cite journal| vauthors = Busker RW, van Henegouwen GM, Kwee BM, Winkens JH |title=Photobinding of flunitrazepam and its major photo-decomposition product N-desmethylflunitrazepam|journal=International Journal of Pharmaceutics|date=May 1987|pages=113–120|volume=36|issue=2–3|doi=10.1016/0378-5173(87)90145-1}}{{cite journal | vauthors = Coller JK, Somogyi AA, Bochner F | title = Quantification of flunitrazepam's oxidative metabolites, 3-hydroxyflunitrazepam and desmethylflunitrazepam, in hepatic microsomal incubations by high-performance liquid chromatography | journal = Journal of Chromatography. B, Biomedical Sciences and Applications | volume = 719 | issue = 1–2 | pages = 87–92 | date = November 1998 | pmid = 9869368 | doi = 10.1016/S0378-4347(98)00383-1 }}{{cite journal | vauthors = Kilicarslan T, Haining RL, Rettie AE, Busto U, Tyndale RF, Sellers EM | title = Flunitrazepam metabolism by cytochrome P450S 2C19 and 3A4 | journal = Drug Metabolism and Disposition | volume = 29 | issue = 4 Pt 1 | pages = 460–5 | date = April 2001 | pmid = 11259331 | url = http://dmd.aspetjournals.org/content/29/4/460.long }} and has been sold online as a designer drug.{{cite journal | vauthors = Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V | title = Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines - an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam and nitrazolam | journal = Journal of Mass Spectrometry | volume = 51 | issue = 11 | pages = 1080–1089 | date = November 2016 | pmid = 27535017 | doi = 10.1002/jms.3840 | bibcode = 2016JMSp...51.1080M }}{{cite journal | vauthors = Katselou M, Papoutsis I, Nikolaou P, Spiliopoulou C, Athanaselis S | title = Metabolites replace the parent drug in the drug arena. The cases of fonazepam and nifoxipam | journal = Forensic Toxicology | volume = 35 | issue = 1 | pages = 1–10 | date = 2016 | pmid = 28127407 | pmc = 5214877 | doi = 10.1007/s11419-016-0338-5 }} It has an IC₅₀ value of 1.499 nM for the GABA_A receptor.{{cite journal | vauthors = Maddalena DJ, Johnston GA | title = Prediction of receptor properties and binding affinity of ligands to benzodiazepine/GABAA receptors using artificial neural networks | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 4 | pages = 715–24 | date = February 1995 | pmid = 7861419 | doi = 10.1021/jm00004a017 }}{{cite journal | vauthors = So SS, Karplus M | title = Genetic neural networks for quantitative structure-activity relationships: improvements and application of benzodiazepine affinity for benzodiazepine/GABAA receptors | journal = Journal of Medicinal Chemistry | volume = 39 | issue = 26 | pages = 5246–56 | date = December 1996 | pmid = 8978853 | doi = 10.1021/jm960536o }}