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HCID 3380Erstellt: 4. November 2026

5-(2-Fluorphenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiaze-pin-2-on

Rohypnol · Primum · Silece · Roipnol · Narcozep · FlunipaM · RO 5-4200 · Flnitrazepam

https://huagongshe.com/de/chemical/3380

Molekülstruktur von 5-(2-Fluorphenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiaze-pin-2-on

Identifikatoren & physikalische Daten

CAS No.1622-62-4
SummenformelC16H12FN3O3
Durchschnittliche Molmasse313,28 g/mol
Monoisotopische Masse313,08626942 g/mol
SMILESCN1C(=O)CN=C(c2ccccc2F)c2cc([N+](=O)[O-])ccc21
InChIKeyPPTYJKAXVCCBDU-UHFFFAOYSA-N
PubChem CID3380
ChEMBLCHEMBL13280
ChEBICHEBI:31622
EC No.216-597-8
DTXSIDDTXSID7023065
Lokaler Name5-(2-Fluorphenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiaze-pin-2-on

Chemische & physikalische Eigenschaften

XLogP2,1
Polarare Oberfläche (TPSA)78,5
H-Brücken-Donoren0
H-Brücken-Akzeptoren5
Frei drehbare Bindungen1
Schwere Atome23
Formalladung0
Komplexität519
ArzneimittelDEA NFLIS-Drug Category -> BenzodiazepinesDEA Schedule IV Controlled Substance -> DepressantsPharmaceuticals -> Nervous system -> AnxiolyticsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Benzodiazepines
LogP (Verteilungskoeffizient)log Kow = 2.062.05
Color/FormPale yellow needles from methylene chloride-hexane
Löslichkeit8.58e-03 g/L45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1 mg/mL
Human DrugsBreast FeedingLactationMilk, HumanHypnotics and SedativesAnti-Anxiety AgentsBenzodiazepinesPharmaceuticals
DecompositionWhen heated to decomposition it emits toxic fumes of /fluoride & nitrogen oxides/.
Schmelzpunkt166-167 °CAlso reported as crystals from acetonitrile and methanolmelting point: 170-72 °C.166 - 167 °C166-167°mp 170-172°
Physical DescriptionSolid
Stability/Shelf LifeStudy has been undertaken to determine the stability of four benzodiazepines: clonazepam, midazolam, flunitrazepam & oxazepam in whole blood samples. Spiked blood was stored at four different temperatures (room temperature, 4 degrees C, -20 degrees C & -80 degrees C) & analysed at selected times during 1 yr. Determination was performed on the first, third & seventh day during the first wk, then once/wk for 3 wk, once every 2 wk for 4 wk, then once/month for 4 months & finally, once every 2 months. Extraction was performed using liquid-liquid extraction with 1-chlorobutane, while quantification was carried out using high performance liquid chromatography equipped with a photodiode-array ultraviolet detector. At room temperature, the concn of all benzodiazepines decreased over 1 yr to 100 & 70% for low & high concns, respectively. At 4 °C, the decr was between 90 & 100% for low concns & between 50 & 80% for high concns. At -20 °C, the measured decr was between 10 & 20% for high & low concns, respectively. At -80 °C, the measured loss was not significant at high concn except for midazolam. However, at low concn the determined decr was between 5 & 12%. The data collected suggests that quantitative results concerning long-term stored samples should be interpreted with caution in forensic cases. Further investigations concerning the stability of drugs in whole blood or other biological samples, additional methods of identification & determination as well as the establishment of optimal storage conditions should be undertaken in forensic cases.
Collision Cross Section168.6 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]
Other Experimental PropertiesWhen mixed in drinks ... colorless, tasteless, odorless ... manufactured now as an oblong olive green tablet with a speckled blue core that when dissolved in light-colored /drinks/ will dye the liquid blue. Generic versions may not contain the dye
Siedepunkt540.9±50.0 °C(Predicted)
Dichte1.3720 (estimate)
Flammpunkt11 °C
Lagerbedingungen2-8°C
pKa (Säurekonstante)pKa 1.8 (Uncertain)
AggregatzustandA neat solid
Henry-Konstante4.3×105 mol/(m3Pa) at 25℃, HSDB (2015)
EPA chemische Informationen2H-1,4-Benzodiazepin-2-one, 5-(2-fluorophenyl)-1,3-dihydro-1-methyl-7-nitro- (1622-62-4)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P319, P330, P337+P317, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 102 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische InformationenDEA schedule IV controlled substance2H-1,4-Benzodiazepin-2-one, 5-(2-fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-: Does not have an individual approval but may be used under an appropriate group standard
FDA-AnforderungenSchedule IV shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. Depressants. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation which contains any quantity of the following substances, including its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation: Flunitrazepam (DEA Code Number: 2763) is included on this list.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
KörperbelastungFollowing a single 2 mg oral dose in five patients, mean milk:plasma ratios at 11, 15, 27, and 39 hr were 0.61, 0.68, 0.9, and 0.75, respectively.
TreatmentGeneral supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.

Anwendungen & Verwendung

Verwenden

Flunitrazepam is used as an hypnotic. This is a controlled substance (depressant).

Wechselwirkungen... The study was conducted/ to determine if the reported clinical adverse interaction of flunitrazepam and buprenorphine was caused by inhibition of drug metabolism. ...: Inhibition of flunitrazepam metabolism by buprenorphine and norbuprenorphine were determined in three human liver microsome preparations carrying the CYP2C19*1/*1 allele. Omeprazole metabolism mediated by CYP2C19 and CYP3A4 was used as a control reaction. Apparent K(i) values were determined. ... Norbuprenorphine did not inhibit the metabolism of flunitrazepam or omeprazole. Buprenorphine inhibited the formation of CYP3A4-mediated pathways of 3-hydroxyflunitrazepam and omeprazole sulfone formation (K(i) 118 and 16 microM) in human liver microsomes. Corresponding values were 38 and 90 microM in cDNA-expressed CYP3A4 microsomes. Projected in vivo inhibition of CYP3A4-mediated metabolism of flunitrazepam by buprenorphine is 0. 1%-2.5%. Estimated inhibition of buprenorphine N-dealkylation by flunitrazepam in vivo is 0.08%. ... The clinical interaction of flunitrazepam and buprenorphine is likely based on a pharmacodynamic mechanism.High doses of Rohypnol particularly when combined with CNS depressant drugs (e.g., alcohol and heroin) can cause severe sedation, unconsciousness, slow heart rate, and suppression of respiration which may be sufficient to result in death.Single iv doses of aminophylline 1-2 mg/kg may reverse the sedation induced by ... flunitrazepam ... .
Gesundheitliche AuswirkungenThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 2.06(2) and a regression-derived equation(3), indicates that flunitrazepam is expected to have moderate mobility in soil(SRC). Volatilization of flunitrazepam from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Flunitrazepam is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.0X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Biodegradation data in soil were not available(SRC, 2013).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 2.06(2) and a regression-derived equation(3), indicates that flunitrazepam is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 2.3X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(5), an estimated BCF of 11(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2013).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), flunitrazepam, which has an estimated vapor pressure of 6.0X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase flunitrazepam may be removed from the air by wet and dry deposition(SRC). Flunitrazepam contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
Expositionspfade50% (suppository) and 64-77% (oral)
Milk ConcentrationsEXPERIMENTAL: Flunitrazepam is excreted into breast milk. Following a single 2 mg oral dose in five patients, mean milk:plasma ratios at 11, 15, 27, and 39 hr were 0.61, 0.68, 0.9, and 0.75, respectively.
ToxizitätsübersichtBenzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Signs and SymptomsSymptoms of overdose include confusion, coma, impaired coordination, sleepiness, and slowed reaction time.
Effluent ConcentrationsFlunitrazepam has been detected, not quantified in unspecified US wastewaters reported in a survey of the 25 most frequently identified but not non-medically used controlled substances(1).
Soil Adsorption/MobilityThe Koc of flunitrazepam is estimated as 170(SRC), using a log Kow of 2.06(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that flunitrazepam is expected to have moderate mobility in soil.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Low, medium, and high doses of flunitrazepam were tested in three independent randomized, double-blind, balanced cross-over, placebo-controlled trials to study the influence of rate of onset of effects and dose administered on its acute effects. Three groups of 12 healthy male volunteers received six oral doses of placebo or flunitrazepam in slow and fast onset conditions as follows: six capsules of 0.16 mg (slow) and a single capsule of 0.8 mg (fast) in the low dose trialsix 0.25 mg (slow) and a single 1.25 mg (fast) capsules for medium doseand six 0.4 mg (slow) and a single 2 mg (fast) capsule for high dose. At each dose level, slow or fast increasing flunitrazepam plasma concentrations lead to similar peak levels, but induced differential subjective and behavioral effects. In addition to objective and subjective sedation, flunitrazepam induced some pleasurable feelings, which were more intense in the fast than in the slow conditions. At the highest dose, unpleasant sedative effects surmounted positive effects, while at the lowest dose pleasurable effects were of low intensity. At the medium dose, the balance between pleasurable and unpleasant feelings resulted in euphorigenic effects, which were evident in the fast condition but were blunted in the slow condition./HUMAN EXPOSURE STUDIES/ This study was designed to explore whether differences in the psychomotor, subjective and memory effects of different benzodiazepines (BDZ) relate to differences in their potencies. Two BDZs with similar kinetics but different potencies were compared. Flunitrazepam (0.5 and 1.0mg, nitrazepam (5 and 10mg) or placebo were administered to 50 healthy volunteers in a double-blind, parallel group design. Subjects completed a test battery before and 1.5 hr post-treatment. The higher dose of the more potent BDZ, flunitrazepam, impaired episodic memory in relation to placebo. In contrast, differences in psychomotor and subjective effects between BDZ were less clear. We conclude that a main caveat to the conclusion that potency plays a role in determining BDZ amnestic effects is the possible contribution of sedation and differential task sensitivities to apparent differential effects of BDZ compounds./SIGNS AND SYMPTOMS/ High doses of Rohypnol particularly when combined with CNS depressant drugs (e.g., alcohol and heroin) can cause severe sedation, unconsciousness, slow heart rate, and suppression of respiration which may be sufficient to result in death./SIGNS AND SYMPTOMS/ Rohypnol causes muscle relaxation. Adverse physical effects include slurred speech, loss of motor coordination, weakness, headache, and respiratory depression. Rohypnol also can produce physical dependence when taken regularly over a period of time.For more Human Toxicity Excerpts (Complete) data for FLUNITRAZEPAM (10 total), please visit the HSDB record page.
Wassergefährdungsklasse (WGK)2
UN-TransportnummerUN 1230 3/PG 2
RTECS-Nr.DF2385000
R-Sätze (R)22-36-39/23/24/25-23/24/25-11
GefahrensymboleXn,T,F
Sicherheitshinweise (S)7-16-36/37-45-36-26
Gefahrenklasse6.1(b)
VerpackungsgruppeIII
Gefahrstoffdaten1622-62-4(Hazardous Substances Data)