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Nifoxipam

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From Wikipedia, the free encyclopedia

Benzodiazepine designer drug

Pharmaceutical compound

Nifoxipam
Legal status


Legal status	AU: Unscheduled BR: Class B1 (Psychoactive drugs) CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act US: Unscheduled UN: Unscheduled In general legal for medical and research uses.
Identifiers
IUPAC name 5-(2-fluorophenyl)-3-hydroxy-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one
CAS Number	74723-10-7
PubChemCID	3058221
ChemSpider	2319383
UNII	9O6C9M3CH6
CompTox Dashboard(EPA)	DTXSID80996250
ECHA InfoCard	100.440.630
Chemical and physical data
Formula	C₁₅H₁₀FN₃O₄
Molar mass	315.260 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1C(O)N=C(C2=CC=CC=C2F)C3=CC([N+]([O-])=O)=CC=C3N1
InChI 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 abenzodiazepine that is a minormetabolite offlunitrazepam and has been sold online as adesigner drug.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]

Nifoxipam produces strong tranquillising and sleep-prolonging effects and has much lower toxicity compared tolormetazepam and flunitrazepam in mice.^[1]

References

[edit]

^^a ^bEP 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 fromthe original on 2016-11-01. Retrieved2016-07-08.
^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. Retrieved15 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.

v t e Benzodiazepines
1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam BMS-906024* Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Cloniprazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Difludiazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine* Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitemazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro05-4082 Ro5-4864* Ro07-5220 Ro07-9749 Ro20-8065 Ro20-8552 SH-I-048A Sulazepam Temazepam Tetrazepam Tifluadom* Timelotem* Tolufazepam Triflunordazepam Tuclazepam Uldazepam
1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam
2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam
Triazolobenzodiazepines	Adinazolam Alprazolam Balovaptan* Bromazolam Clonazolam Estazolam Fluadinazolam Flualprazolam Flubromazolam Flunitrazolam Nitrazolam Phenazolam Pyrazolam Rilmazolam (active metabolite ofRilmazafone) Triazolam
Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil GL-II-73 Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F
Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam
Thienodiazepines	Bentazepam Clotiazepam Ro09-9212
Thienotriazolodiazepines	α-Hydroxyetizolam Apafant* Brotizolam Ciclotizolam Clotizolam Deschloroclotizolam Deschloroetizolam Etizolam Flubrotizolam Fluclotizolam Fluetizolam Israpafant* JQ1* Metizolam
Thienobenzodiazepines*	Olanzapine Telenzepine
Pyridodiazepines	Lopirazepam
Pyridotriazolodiazepines	Zapizolam
Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*
Pyrrolodiazepines	Premazepam
Tetrahydroisoquinobenzodiazepines	Clazolam
Pyrrolobenzodiazepines*	Anthramycin
Benzodiazepine prodrugs	Alprazolam triazolobenzophenone Avizafone Rilmazafone
* atypical activity profile (notGABA_A receptor ligands)

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neurosteroids	Acebrochol Alfadolone Alfaxolone Brexanolone (allopregnanolone) Eltanolone (pregnanolone) Ganaxolone Hydroxydione Minaxolone Progesterone Renanolone Zuranolone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pagoclone Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Cipepofol (ciprofol) Fospropofol Propofol Propofol hemisuccinate
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol (THIP) Ibotenic acid (Amanita muscaria) Kavalactones Loreclezole Muscimol (Amanita muscaria) Paraldehyde Petrichloral Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine

Melatonin

Orexin

α₂δ VDCC

Others

Cannabinoids (e.g.,cannabis,tetrahydrocannabinol/dronabinol,nabilone,cannabidiol,Zenivol)
Chlorophenylalkyldiols
Diethylpropanediol
Evoxine
Fenadiazole
GABA reuptake inhibitors (e.g.,tiagabine)
Guaifenesin-relatedmuscle relaxants
Midaflur
Opioids (e.g.,morphine)
Passion flower
Phemerazole
Scopolamine
Serotonin precursors (e.g.,tryptophan,5-hydroxytryptophan (5-HTP;oxitriptan))
Trazodone
UMB68
Valnoctamide

v t e GABA_A receptor positive modulators
Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g.,baicalin) Wogonin
Imidazoles	Etomidate Metomidate Methoxyetomidate Propoxate Isopropoxate Butomidate Iso-butomidate Sec-butomidate CF2-Etomidate CF3-Etomidate CF3-Propoxate Flutomidate 2,6-Dichloro-3-fluoroetomidate
Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certainanabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Posovolone Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone
Nonbenzodiazepines	Cyclopyrrolones:Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines:Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines:Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others:Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) Miltirone (rosmariquinone) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Cipepofol Fospropofol Propofol Propofol hemisuccinate Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
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 Nicotinic acid Nicotinamide 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) Unsorted benzodiazepine site positive modulators:α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also:Receptor/signaling modulators •GABA receptor modulators •GABA metabolism/transport modulators

Glycine receptor modulators

Receptor
(ligands)

GlyRTooltip 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

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 andpicrotoxinin)
PMBA
Riluzole
Tropeines (e.g.,bemesetron,LY-278584,tropisetron,zatosetron)
Verapamil
Zinc

NMDARTooltip N-Methyl-D-aspartate receptor

Seehere instead.

Transporter
(blockers)

GlyT1Tooltip Glycine transporter 1	ACPPB ALX-5407 (NFPS) ASP2535 Bitopertin (RG1678/RO4917838) CP-802079 Ethanol (alcohol) Glycyldodecylamide GSK1018921 Iclepertin LY-2365109 Mardepodect ORG-24598 ORG-25935 (SCH-900435) Pesampator (BIIB-104, PF-04958242) PF-03463275 Sarcosine SNG-12 (Synapsinae) SSR-103,800 SSR-504,734 Tilapertin
GlyT2Tooltip Glycine transporter 2	ALX-1393 Amoxapine Ethanol (alcohol) NAGly Opiranserin (VVZ-149) ORG-25543 VVZ-368

See also: Receptor/signaling modulators; GABA receptor modulators; GABA_A receptor positive modulators; Ionotropic glutamate receptor modulators

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