Desmethylflunitrazepam

Desmethylflunitrazepam
Systematic (IUPAC) name

5-(2-fluorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
Clinical data
Legal status	CA: Schedule IV
Identifiers
CAS Number	2558-30-7
PubChem	CID 520217
ChemSpider	453770
Chemical data
Formula	C₁₅H₁₀FN₃O₃
Molar mass	299.26 g·mol⁻¹
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

Desmethylflunitrazepam (Ro05-4435, fonazepam) is a benzodiazepine that is a metabolite of flunitrazepam.^[1]^[2]^[3] It has an IC₅₀ value of 1.499 nM for the GABA_A receptor.^[4]^[5]

References

↑ Ruud W. Busker, Gerard M.J.Beijersbergen van Henegouwen, Brigitta M.C. Kwee, Jos H.M. Winkens (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.
↑ Janet K Coller, Andrew A Somogyi, Felix Bochner (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.
↑ Tansel Kilicarslan, Robert L. Haining, Allan E. Rettie, Usanda Busto, Rachel F. Tyndale, Edward M. Sellers (April 2001). "Flunitrazepam Metabolism by Cytochrome P450s 2C19 and 3A4". Drug Metabolism and Disposition 29 (4): 460–465. PMID 11259331.
↑ Desmond J. Maddalena, Graham A. R. Johnston (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): 715–724. doi:10.1021/jm00004a017. PMID 7861419.
↑ Sung-Sau So, Martin Karplus (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): 5246–5256. doi:10.1021/jm960536o. PMID 8978853.

Benzodiazepines

1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam 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 Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro5-4864* Sulazepam Temazepam Tetrazepam Tifluadom* 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 Clonazolam Estazolam Flubromazolam Nitrazolam Pyrazolam Triazolam

Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil 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

Thienotriazolodiazepines	Brotizolam Ciclotizolam Desmethyletizolam Etizolam Israpafant* JQ1*

Thienobenzodiazepines*	Olanzapine Telenzepine

Pyridodiazepines	Lopirazepam

Pyridotriazolodiazepines	Zapizolam

Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*

Pyrrolodiazepines	Premazepam

Tetrahydroisoquinobenzodiazepines	Clazolam

Pyrrolobenzodiazepines*	Anthramycin

Benzodiazepine prodrugs	Avizafone Rilmazafone

* atypical activity profile (not GABA_A receptor ligands)

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol Alcohol Ethchlorvynol Methylpentynol Trichloroethanol

Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Vinbarbital Vinylbital

Benzodiazepines	Brotizolam Cinolazepam Climazolam Doxefazepam Estazolam Flunitrazepam Flurazepam Flutoprazepam Haloxazolam Loprazolam Lormetazepam Midazolam Nimetazepam Nitrazepam Phenazepam 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

Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone

Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone

Phenols	Fospropofol Propofol

Piperidinediones	Glutethimide Methyprylon Pyrithyldione Piperidione

Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone

Volatiles/gases	Acetophenone Acetylglycinamide chloral hydrate Centalun Chloral betaine Chloral hydrate Paraldehyde

Others	Bromide compounds Lithium bromide Potassium bromide Sodium bromide Chloralose Clomethiazole Dichloralphenazone Gaboxadol Loreclezole Kava constituents Kavalactones Petrichloral Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos Valerian constituents Isovaleramide Isovaleric acid Valerenic acid

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Pheniramine Promethazine Propiomazine

Antidepressants	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

Others

GABA_A receptor positive allosteric modulators

Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (drinking alcohol) 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 CP-1414S 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 Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam 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 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 Propoxate

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 Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP Etiocholanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-217 SAGE-689 THDOC

Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423; 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 JM-1232 L-838,417 Lirequinil (Ro41-3696) 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	Fospropofol Propofol 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 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL 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 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Nicotinamide (niacinamide) Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal SAGE-547 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 PAMs: MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: GABAergics

Glycinergics

Receptor
(ligands)

GlyR

PAMs: Alcohols (e.g., brometone, chlorobutanol (chloretone), ethanol, 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

NAMs: 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

Transporter
(blockers)

GlyT1	ACPPB ALX-1393 ALX-5407 (NFPS) AMG-747 ASP2535 Bitopertin (RG1678/RO4917838) CP-802079 Ethanol Glycyldodecylamide GSK1018921 LY-2365109 Org 24598 Org 25935 (SCH-900435) PF-02545920 PF-03463275 PF-04958242 Sarcosine SSR-103,800 SSR-504,734

GlyT2	Amoxapine Ethanol NAGly Org 25543

Others

Precursors: 3-PG
GHB
L-Serine
L-Theonine

Cofactors: Vitamin B₆

See also: GABAergics • GHBergics • Glutamatergics

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