Nifoxipam

{{Short description|Benzodiazepine designer drug}}

{{Drugbox

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

| image = Nifoxipam.svg

| image_class = skin-invert-image

| width = 222

| image2 = Nifoxipam ball-and-stick model.png

| width2 = 200

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = Unscheduled

| legal_BR = B1

| legal_CA = Schedule IV

| legal_DE = NpSG

| legal_UK = PSA

| legal_US = Unscheduled

| legal_UN = Unscheduled

| legal_status = In general legal for medical and research uses.

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 74723-10-7

| ATC_prefix =

| ATC_suffix =

| PubChem = 3058221

| ChemSpiderID = 2319383

| UNII = 9O6C9M3CH6

| C=15 | H=10 | F=1 | N=3 | O=4

| melting_point =

| smiles = O=C1C(O)N=C(C2=CC=CC=C2F)C3=CC([N+]([O-])=O)=CC=C3N1

| StdInChI = 1S/C15H10FN3O4/c16-11-4-2-1-3-9(11)13-10-7-8(19(22)23)5-6-12(10)17-14(20)15(21)18-13/h1-7,15,21H,(H,17,20)

| StdInChIKey = UHFIFTRHLBAWGY-UHFFFAOYSA-N

}}

Nifoxipam (3-hydroxydesmethylflunitrazepam, DP 370) is a benzodiazepine that is a minor metabolite of flunitrazepam and has been sold online as a designer drug.{{cite patent | country = EP | number = 0158267 | title = Pharmaceutical composition containing 5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-7-nitro- or 5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-one and process for their preparation | pubdate = 16 October 1985 | inventor = Posselt K, Wagener HH, Gruber K, | assign1 = Dolorgiet Beteiligungs-GmbH }}{{cite web | url=http://nsddb.eu/substance/478/ | title=Nifoxipam | publisher=New Synthetic Drugs Database | access-date=2016-07-08 | archive-date=2016-11-01 | archive-url=https://web.archive.org/web/20161101121906/http://nsddb.eu/substance/478/ | url-status=dead }}{{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 }}{{cite journal | vauthors = Moosmann B, King LA, Auwärter V | title = Designer benzodiazepines: A new challenge | journal = World Psychiatry | volume = 14 | issue = 2 | pages = 248 | date = June 2015 | pmid = 26043347 | pmc = 4471986 | doi = 10.1002/wps.20236 }}{{cite web | url=http://www.kfx.org.uk/drug_facts/drug_facts_images_and_pdfs/researchchemicals_4.2015.pdf | title=Drug Facts - Newer Unregulated Drugs | publisher=KFx | date=August 2015 | access-date=15 August 2015 | author=Kevin Flemen}}{{cite web | url=http://www.wedinos.org/db/materials/view/00713 | title=Nifoxipam | publisher=WEDINOS}}{{cite journal | vauthors = Meyer MR, Bergstrand MP, Helander A, Beck O | s2cid = 25831532 | title = Identification of main human urinary metabolites of the designer nitrobenzodiazepines clonazolam, meclonazepam, and nifoxipam by nano-liquid chromatography-high-resolution mass spectrometry for drug testing purposes | journal = Analytical and Bioanalytical Chemistry | volume = 408 | issue = 13 | pages = 3571–91 | date = May 2016 | pmid = 27071765 | doi = 10.1007/s00216-016-9439-6 }}{{cite journal | vauthors = Pettersson Bergstrand M, Helander A, Hansson T, Beck O | title = Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays | journal = Drug Testing and Analysis | volume = 9 | issue = 4 | pages = 640–645 | date = April 2017 | pmid = 27366870 | doi = 10.1002/dta.2003 }}{{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 }}

Nifoxipam produces strong tranquillising and sleep-prolonging effects and has much lower toxicity compared to lormetazepam and flunitrazepam in mice.