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Benzodiazepine designer drug
Pharmaceutical compound
Nifoxipam Legal status
5-(2-fluorophenyl)-3-hydroxy-7-nitro-2,3-dihydro-1H -1,4-benzodiazepin-2-one
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 15 H 10 F N 3 O 4 Molar mass −1 3D model (JSmol )
O=C1C(O)N=C(C2=CC=CC=C2F)C3=CC([N+]([O-])=O)=CC=C3N1
InChI=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)
Key: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 .[ 1] [ 2] [ 3] [ 4] [ 5] [ 6] [ 7] [ 8] [ 9]
Nifoxipam produces strong tranquillising and sleep-prolonging effects and has much lower toxicity compared to lormetazepam and flunitrazepam in mice.[ 1]
^ a b EP 0158267 , Posselt K, Wagener HH, Gruber K,, "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", published 16 October 1985, assigned to Dolorgiet Beteiligungs-GmbH ^ "Nifoxipam" . New Synthetic Drugs Database. Archived from the original on 2016-11-01. Retrieved 2016-07-08 .^ 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 . ^ Moosmann B, King LA, Auwärter V (June 2015). "Designer benzodiazepines: A new challenge" . World Psychiatry . 14 (2): 248. doi :10.1002/wps.20236 . PMC 4471986 PMID 26043347 . ^ Kevin Flemen (August 2015). "Drug Facts - Newer Unregulated Drugs" (PDF) . KFx. Retrieved 15 August 2015 . ^ "Nifoxipam" . WEDINOS.^ Meyer MR, Bergstrand MP, Helander A, Beck O (May 2016). "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". Analytical and Bioanalytical Chemistry . 408 (13): 3571–91. doi :10.1007/s00216-016-9439-6 . PMID 27071765 . S2CID 25831532 . ^ Pettersson Bergstrand M, Helander A, Hansson T, Beck O (April 2017). "Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays". Drug Testing and Analysis . 9 (4): 640–645. doi :10.1002/dta.2003 . PMID 27366870 . ^ 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 .
Alcohols Barbiturates Benzodiazepines Carbamates Flavonoids Imidazoles Kava constituentsMonoureides Neuroactive steroids Nonbenzodiazepines Phenols Piperidinediones Pyrazolopyridines Quinazolinones Volatiles /gases Others/unsorted
3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g., ivermectin )Bromide compounds (e.g., lithium bromide , potassium bromide , sodium bromide )Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g., dihydroergocryptine , dihydroergosine , dihydroergotamine , ergoloid (dihydroergotoxine) )DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid , mefenamic acid , niflumic acid , tolfenamic acid )Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol , honokiol , magnolol , obovatol )Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Niacinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) , tetronal , trional )Terpenoids (e.g., borneol )Topiramate Valerian constituents (e.g., isovaleric acid , isovaleramide , valerenic acid , valerenol )
Receptor (ligands )
GlyR Tooltip Glycine receptor
Positive modulators: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol (alcohol) , tert -butanol (2M2P)tribromoethanol , trichloroethanol , trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g., pentobarbital , sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine )Etomidate Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone , pregnenolone (eltanolone) , pregnenolone acetate , minaxolone , ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine , bemesetron , cocaine , LY-278584 , tropisetron , zatosetron )Volatiles /gases (e.g., chloral hydrate , chloroform , desflurane , diethyl ether (ether) , enflurane , halothane , isoflurane , methoxyflurane , sevoflurane , toluene , trichloroethane (methyl chloroform) , trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG , anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline , 4-hydroxyquinoline-3-carboxylic acid , 5,7-CIQA , 7-CIQ , 7-TFQ , 7-TFQA )RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam , clonazepam , diazepam , flunitrazepam , flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine , nifedipine , nitrendipine )Furosemide Genistein Ginkgo constituents (e.g., bilobalide , ginkgolides (e.g., ginkgolide A , ginkgolide B , ginkgolide C , ginkgolide J , ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate , 3β-androsterone sulfate , deoxycorticosterone , DHEA sulfate , pregnenolone sulfate , progesterone )Opioids (e.g., codeine , dextromethorphan , dextrorphan , levomethadone , levorphanol , morphine , oripavine , pethidine , thebaine )Picrotoxin (i.e., picrotin and picrotoxinin )PMBA Riluzole Tropeines (e.g., bemesetron , LY-278584 , tropisetron , zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
