CAS 1622-62-4|Flunitrazepam solution|5-(2-fluorophenyl)-1-methyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one|fluniβ|氟硝西泮溶液|Narcozep|primun|Flunitrazepam|Flunitrazepamum [inn-latin]|Primun...

General Information

Structure

Molecular Formula

C₁₆H₁₂FN₃O₃

Molecular Mass

313.2831832

Exact Mass

313.08626948

Charge

InChI

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

InChIKey

PPTYJKAXVCCBDU-UHFFFAOYSA-N

Canonic Smiles

CN1C(=O)CN=C(c2c1ccc(c2)[N+](=O)[O-])c1ccccc1F

Isomeric Smiles

Fc1c(C2=NCC(=O)N(c3c2cc([N+](=O)[O-])cc3)C)cccc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.55466

LogD (pH = 7.4)

2.554727

Log P

2.554728

Molar Refractivity

82.5482

Polarizability

30.054867

Polar Surface Area

78.49

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.2

LOG S

-4.56

Solubility (Water)

8.58e-03 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Flunitrazepam solution氟硝西泮溶液FlunitrazepamFlunitrazepamum [inn-latin]Ro 5-4200氟硝西泮5-(2-Fluorophenyl)-1-methyl-7-nitro-3H-1,4-benzodiazepin-2(1H)-oneFlunitrazepam7-Nitro-1-methyl-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2(1H)-oneRoipnol5-(2-Fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-oneFluridrazepamFlunipamRohypnolNarcozepSilece5-(o-Fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-oneFlunidazepam5-(2-Fluorophenyl)-1-methyl-7-nitro-1,3-dihydrobenzo[e][1,4]diazepin-2-one

IUPAC name

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

IUPAC Traditional name

fluniβ primun

Brand Name

NarcozepPrimunRohypnolRoipnol

Names and Identifiers

Registration numbers

MDL Number

EC Number

CAS Number

CHEMBL

PubChem CID

KEGG ID

ATC CODE

DrugBank ID

Chemspider ID

Unique Ingredient Identifier

620X0222FQ

Wikipedia Title

Flunitrazepam

PubChem SID

2489499316096478946504553

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.06 [HANSCH,C ET AL. (1995)]

Solubility

ethanol: soluble

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1 mg/mL

DMF: soluble

Safety Information

Warning

DF2385000

P305+P351+P338

22-36

Product Information

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

Molecule Details

DrugBank

DB01544

Drug Groups

illicit; approved

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]

Indication

For short-term treatment of severe insomnias, that are not responsive to other hypnotics.

Pharmacology

Flunitrazepam is a powerful hypnotic drug that is a benzodiazepine derivative. It has powerful hypnotic, sedative, anxiolytic, and skeletal muscle relaxant properties. The drug is sometimes used as a date rape drug. In the United States, the drug has not been approved by the Food and Drug Administration for medical use, and is considered to be an illegal drug. It has however been approved in the United Kingdom and other countries.

Toxicity

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

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

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

Half Life

18-26 hours

References

• 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. [Pubmed]

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

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

• 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. [Pubmed]

• 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. [Pubmed]

External Links

• [Wikipedia]

Wikipedia

Flunitrazepam

Sigma Aldrich

F9261

Biochem/physiol Actions
Hypnotic; anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

TRC

F500700

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

Molecule Details

References

PubChem Literature

From Data Sources

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

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

• 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. Pubmed

• Caplan, Y., et al.: J. Anal. Toxicol., 25, 396 (1963)

• Eidelberg, E., et al.: Neurology, 5, 223 (1963)

• Wood, M., et al.: Forensic Sci. Int., 150, 227 (1963)

• Sternbach, L.H., et al.: J. Med. Chem., 6, 261 (1963)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

fluniβ primun

Brand Name

NarcozepPrimunRohypnolRoipnol

Registration numbers

MDL Number

EC Number

CAS Number

CHEMBL

PubChem CID

KEGG ID

ATC CODE

DrugBank ID

Chemspider ID

Unique Ingredient Identifier

620X0222FQ

Wikipedia Title

Flunitrazepam

PubChem SID

2489499316096478946504553

References

PubChem Literature

From Data Sources

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

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

• 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. Pubmed

• Caplan, Y., et al.: J. Anal. Toxicol., 25, 396 (1963)

• Eidelberg, E., et al.: Neurology, 5, 223 (1963)

• Wood, M., et al.: Forensic Sci. Int., 150, 227 (1963)

• Sternbach, L.H., et al.: J. Med. Chem., 6, 261 (1963)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

2.06 [HANSCH,C ET AL. (1995)]

Solubility

ethanol: soluble

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1 mg/mL

DMF: soluble

Safety Information

Warning

DF2385000

P305+P351+P338

22-36

Product Information

Download link

Molecule Details

DrugBank

DB01544

Drug Groups

illicit; approved

Description

Indication

For short-term treatment of severe insomnias, that are not responsive to other hypnotics.

Pharmacology

Toxicity

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

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

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

Half Life

18-26 hours

References

• 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. [Pubmed]

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

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

External Links

• [Wikipedia]

Wikipedia

Flunitrazepam

Sigma Aldrich

F9261

Biochem/physiol Actions
Hypnotic; anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

TRC

F500700

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

Molecule

ID:1329