ContaminantDB: Flunitrazepam

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (22)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:51 UTC

Update Date

2026-05-14 17:08:00 UTC

Accession Number

CHEM002395

Identification

Common Name

Flunitrazepam

Class

Small Molecule

Description

A benzodiazepine with pharmacologic actions similar to those of diazepam that can cause anterograde amnesia. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug. [PubChem]

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Anti-Anxiety Agent
Benzodiazepine
Drug
GABA Modulator
Human Neurotoxin
Hypnotic and Sedative
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dihydro-5-(O-fluorophenyl)-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-one	ChEBI
1-Methyl-7-nitro-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2(1H)-one	ChEBI
5-(O-Fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-one	ChEBI
Flunidazepam	ChEBI
Fluninoc	ChEBI
Flunipam	ChEBI
Flunita	ChEBI
Flunitrazepamum	ChEBI
Fluridrazepam	ChEBI
Fluscand	ChEBI
Hipnosedon	ChEBI
Hypnodorm	ChEBI
Hypnor	ChEBI
Narcozep	ChEBI
Primum	ChEBI
RO 5-4200	ChEBI
RO-5-4200	ChEBI
RO-54200	ChEBI
RO54200	ChEBI
Rohypnol	ChEBI
Roipnol	ChEBI
Silece	ChEBI
Valsera	ChEBI
1a Brand OF flunitrazepam	HMDB
Flunitrazepam ratiopharm	HMDB
Flunitrazepam-teva	HMDB
Flunitrazepam-neuraxpharm	HMDB
Hexal brand OF flunitrazepam	HMDB
Roche brand OF flunitrazepam	HMDB
Neuraxpharm brand OF flunitrazepam	HMDB
Ratiopharm brand OF flunitrazepam	HMDB
Fluni 1a pharma	HMDB
CT Arzneimittel brand OF flunitrazepam	HMDB
Flunimerck	HMDB
Flunitrazepam teva	HMDB
Flunitrazepam neuraxpharm	HMDB
Flunitrazepam-ratiopharm	HMDB
Rohipnol	HMDB
Teva brand OF flunitrazepam	HMDB
Betapharm brand OF flunitrazepam	HMDB
Flunibeta	HMDB
Merck dura brand OF flunitrazepam	HMDB
CT-Arzneimittel brand OF flunitrazepam	HMDB
Flunizep von CT	HMDB
Von CT, flunizep	HMDB

Chemical Formula

C₁₆H₁₂FN₃O₃

Average Molecular Mass

313.283 g/mol

Monoisotopic Mass

313.086 g/mol

CAS Registry Number

1622-62-4

IUPAC Name

5-(2-fluorophenyl)-1-methyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

flunitrazepam

SMILES

CN1C2=C(C=C(C=C2)[N+]([O-])=O)C(=NCC1=O)C1=CC=CC=C1F

InChI Identifier

InChI=1S/C16H12FN3O3/c1-19-14-7-6-10(20(22)23)8-12(14)16(18-9-15(19)21)11-4-2-3-5-13(11)17/h2-8H,9H2,1H3

InChI Key

PPTYJKAXVCCBDU-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Nitroaromatic compound
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Organic nitro compound
Carboxamide group
Ketimine
Lactam
C-nitro compound
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organopnictogen compound
Imine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organohalogen compound
Carbonyl group
Organofluoride
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	166-167°C
Boiling Point	Not Available
Solubility	8.58e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0086 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.55	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.55 m³·mol⁻¹	ChemAxon
Polarizability	29.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03du-2191000000-6d65c6a7646264996d7c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0009000000-d3cdbd0e6db0ff7d3658	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-02t9-0098000000-ed4fc29ca5e103e7e7ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0292000000-910e58767edf9829ae76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0590000000-f32a6119c0a1af4b09f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0009000000-0917b69ebd96bce7d228	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0009000000-52198b26a21902b1164d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-02t9-0095000000-6905e6ef41a999c5c6bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014r-0291000000-05daa60855227774f98a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01p9-0590000000-1dc724d4ffca2a0dcc87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0230-0970000000-c801330e64d95e44fce8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00si-1920000000-6d855cf670784a504122	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-2910000000-ab0a5646c93755d78538	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gx0-3900000000-0e0998c190e076f40d1b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-02t9-0089000000-cd60ffdaaa581557c2e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-01p9-0590000000-2d293fa78f79ead8809d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-014r-0191000000-8795ce46cab22c3d13f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03di-0009000000-0917b69ebd96bce7d228	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0230-0970000000-36b73fbbe050671180ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-0590000000-2edbc58a7f6027ae8785	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-93aa3b8655f147913878	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0039000000-2c09292b786206e62c27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-07vl-3922000000-a46dddc6a35eee14faf9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-de2d40c51a7b8e4bb054	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009000000-d6e19246eb2e60003f64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9001000000-8593a33f1e3dc94a81c5	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01p9-2393000000-5d873203e4acf1211838	Spectrum

Toxicity Profile

Route of Exposure

50% (suppository) and 64-77% (oral)

Mechanism of Toxicity

Benzodiazepines 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.

Metabolism

Hepatic. Half Life: 18-26 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For short-term treatment of severe insomnias, that are not responsive to other hypnotics. Not approved by the FDA in the U.S. In the U.K. it is used (and available only by private prescription) in some hospitals to sedate patients undergoing colonoscopy. In Norway, flunitrazepam is available as a prescription drug to treat insomnia under the brand name Flunipam 1 mg. [Wikipedia]

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.

Symptoms

Symptoms of overdose include confusion, coma, impaired coordination, sleepiness, and slowed reaction time.

Treatment

General 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.

Concentrations

Not Available

External Links

DrugBank ID

DB01544

HMDB ID

HMDB0015510

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Kariss, J. and Newmark, H.L.; U.S. Patent 3,116,203; December 31, 1963; assigned to Hoffmann-la Roche Inc.  Kariss, J. and Newmark, H.L.; US. Patent 3,123,529; March 3,1964; assigned to Hoffmann-La Roche Inc.  Keiler, O., Steiger, N. and Sternbach, L.H.; U.S. Patent 3,203,990; August 31, 1965; assigned to Hoffmann-La Roche Inc.

MSDS

Not Available

General References

1. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72.

2. Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41.

3. Robertson MD, Drummer OH: Postmortem drug metabolism by bacteria. J Forensic Sci. 1995 May;40(3):382-6.

4. Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5.

5. Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8.

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11393809

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17889

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18070

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19839