Flubromazepam

Last updated
Flubromazepam
Flubromazepam.svg
Clinical data
Routes of
administration
Oral
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 106 hours
Identifiers
  • 7-Bromo-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H10BrFN2O
Molar mass 333.160 g·mol−1
3D model (JSmol)
  • BrC1=CC(C(C2=CC=CC=C2F)=NC3)=C(C=C1)NC3=O
  • InChI=1S/C15H10BrFN2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)
  • Key:ZRKDDZBVSZLOFS-UHFFFAOYSA-N

Flubromazepam is a benzodiazepine derivative which was first synthesized in 1960, [1] but was never marketed and did not receive any further attention or study until late 2012 when it appeared on the grey market as a novel designer drug. [2] [3] [4] [5] [6] [7] [8]

Contents

It is a structural analog of phenazepam in which the chlorine atom has been replaced by a fluorine atom.

An alternate isomer, 5-(2-bromophenyl)-7-fluoro-1,3-dihydro-2H-1,4-benzodiazepin-2-one or "iso-flubromazepam", [9] may have been sold under the same name. [2]

Alternate isomer Flubromazepam isomer.svg
Alternate isomer

United Kingdom

In the UK, flubromazepam has been classified as a Class C drug by the May 2017 amendment to The Misuse of Drugs Act 1971 along with several other designer benzodiazepine drugs. [10]

United States

Flubromazepam, clonazolam, and flubromazolam are Schedule I controlled substances under Virginia State Law. [11]

See also

Related Research Articles

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Phenazepam is a benzodiazepine drug, first developed in the Soviet Union in 1975, and now produced in Russia and some affiliated countries.

<span class="mw-page-title-main">Meclonazepam</span> Chemical compound

Meclonazepam ((S)-3-methylclonazepam) was discovered by a team at Hoffmann-La Roche in the 1970s and is a drug which is a benzodiazepine derivative similar in structure to clonazepam. It has sedative and anxiolytic actions like those of other benzodiazepines, and also has anti-parasitic effects against the parasitic worm Schistosoma mansoni.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.

<i>N</i>-Desalkylflurazepam Benzodiazepine analog

N-Desalkylflurazepam is a benzodiazepine analog and an active metabolite of several other benzodiazepine drugs including flurazepam, flutoprazepam, fludiazepam, midazolam, flutazolam, quazepam, and ethyl loflazepate. It is long-acting, prone to accumulation, and binds unselectively to the various benzodiazepine receptor subtypes. It has been sold as a designer drug from 2016 onward.

<span class="mw-page-title-main">Pyrazolam</span> Benzodiazepine

Pyrazolam (SH-I-04) is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s. It has since been "rediscovered" and sold as a designer drug since 2012.

<span class="mw-page-title-main">Diclazepam</span> Benzodiazepine medication

Diclazepam (Ro5-3448), also known as chlorodiazepam and 2'-chloro-diazepam, is a benzodiazepine and functional analog of diazepam. It was first synthesized by Leo Sternbach and his team at Hoffman-La Roche in 1960. It is not currently approved for use as a medication, but rather sold as an unscheduled substance. Efficacy and safety have not been tested in humans.

<span class="mw-page-title-main">3-Hydroxyphenazepam</span> Benzodiazepine medication

3-Hydroxyphenazepam is a benzodiazepine with hypnotic, sedative, anxiolytic, and anticonvulsant properties. It is an active metabolite of phenazepam, as well as the active metabolite of the benzodiazepine prodrug cinazepam. Relative to phenazepam, 3-hydroxyphenazepam has diminished myorelaxant properties, but is about equivalent in most other regards. Like other benzodiazepines, 3-hydroxyphenazepam behaves as a positive allosteric modulator of the benzodiazepine site of the GABAA receptor with an EC50 value of 10.3 nM. It has been sold online as a designer drug.

<span class="mw-page-title-main">Clonazolam</span> Benzodiazepine derivative research chemical

Clonazolam is a drug of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. Little research has been done about its effects and metabolism, and is sold online as a designer drug.

<span class="mw-page-title-main">Flubromazolam</span> Triazolobenzodiazepine/Benzodiazepine derivative

Flubromazolam (JYI-73) is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives. Flubromazolam is reputed to be highly potent, and concerns have been raised that clonazolam and flubromazolam in particular may pose comparatively higher risks than other designer benzodiazepines, due to their ability to produce strong sedation and amnesia at oral doses of as little as 0.5 mg. Life-threatening adverse reactions have been observed at doses of only 3 mg of flubromazolam.

<span class="mw-page-title-main">Deschloroetizolam</span> Chemical compound

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<span class="mw-page-title-main">Nifoxipam</span> Benzodiazepine designer drug

Nifoxipam is a benzodiazepine that is a minor metabolite of flunitrazepam and has been sold online as a designer drug.

<span class="mw-page-title-main">Metizolam</span> Chemical compound

Metizolam is a thienotriazolodiazepine that is the demethylated analogue of the closely related etizolam.

<span class="mw-page-title-main">Desmethylflunitrazepam</span> Chemical compound

Desmethylflunitrazepam (also known as norflunitrazepam, Ro05-4435 and fonazepam) is a benzodiazepine that is a metabolite of flunitrazepam and has been sold online as a designer drug. It has an IC50 value of 1.499 nM for the GABAA receptor.

<span class="mw-page-title-main">Nitrazolam</span> Benzodiazepine designer drug

Nitrazolam is a triazolobenzodiazepine (TBZD) , which are benzodiazepine (BZD) derivatives, that has been sold online as a designer drug.

<span class="mw-page-title-main">Cloniprazepam</span> Benzodiazepine drug

Cloniprazepam is a benzodiazepine derivative and a prodrug of clonazepam, 7-aminoclonazepam, and other metabolites.

<span class="mw-page-title-main">CUMYL-PEGACLONE</span> Chemical compound

CUMYL-PEGACLONE (SGT-151) is a gamma-carboline based synthetic cannabinoid that has been sold as a designer drug. The gamma-carboline core structure seen in CUMYL-PEGACLONE had not previously been encountered in a designer cannabinoid, though it is similar in structure to other gamma-carboline cannabinoids disclosed by Bristol-Myers Squibb in 2001.

<span class="mw-page-title-main">Flualprazolam</span> Chemical compound

Flualprazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It was first synthesised in 1976, but was never marketed. It can be seen as the triazolo version of fludiazepam. It has subsequently been sold as a designer drug, first being definitively identified as such in Sweden in 2018. It can be described as the 2'-fluoro derivative of alprazolam or the fluoro instead of chloro analogue of triazolam, and has similar sedative and anxiolytic effects.

<span class="mw-page-title-main">Nitemazepam</span> Benzodiazepine designer drug

Nitemazepam is a benzodiazepine derivative which was first synthesised in the 1970s but was never marketed. It is the 7-nitro instead of 7-chloro analogue of temazepam, and also the 3-hydroxy derivative of nimetazepam, and an active metabolite. It has in more recent years been sold as a designer drug, first being definitively identified in Europe in 2017. It is metabolized to 7-aminonitemazepam, nimetazepam, 3-hydroxynitemazepam, temazepam, and nimetazepam glucuronide.

<span class="mw-page-title-main">EG-018</span> Chemical compound

EG-018 is a carbazole-based synthetic cannabinoid that has been sold online as a designer drug. It acts as a partial agonist of the CB1 and CB2 receptor, with reasonably high binding affinity, but low efficacy in terms of inducing a signaling response.

References

  1. US 3136815,"Amino substituted benzophenone oximes and derivatives thereof"
  2. 1 2 Moosmann B, Huppertz LM, Hutter M, Buchwald A, Ferlaino S, Auwärter V (November 2013). "Detection and identification of the designer benzodiazepine flubromazepam and preliminary data on its metabolism and pharmacokinetics". Journal of Mass Spectrometry. 48 (11): 1150–9. Bibcode:2013JMSp...48.1150M. doi:10.1002/jms.3279. PMID   24259203.
  3. Moosmann B, Hutter M, Huppertz LM, Auwärter V. "Characterization of the designer benzodiazepines pyrazolam and flubromazepam and study on their detectability in human serum and urine samples" (PDF). Institute of Forensic Medicine, Forensic Toxicology, University Medical Center Freiburg, Freiburg, Germany.
  4. O'Connor LC, Torrance HJ, McKeown DA (March 2016). "ELISA Detection of Phenazepam, Etizolam, Pyrazolam, Flubromazepam, Diclazepam and Delorazepam in Blood Using Immunalysis® Benzodiazepine Kit". Journal of Analytical Toxicology. 40 (2): 159–61. doi: 10.1093/jat/bkv122 . PMID   26518230.
  5. "Flubromazepam". New Synthetic Drugs Database. 12 November 2023.
  6. 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.
  7. Høiseth G, Tuv SS, Karinen R (November 2016). "Blood concentrations of new designer benzodiazepines in forensic cases". Forensic Science International. 268: 35–38. doi:10.1016/j.forsciint.2016.09.006. PMID   27685473.
  8. Manchester KR, Maskell PD, Waters L (March 2018). "a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances" (PDF). Drug Testing and Analysis. doi:10.1002/dta.2387. PMID   29582576. S2CID   31098917.
  9. Baumeister D, Tojo LM, Tracy DK (April 2015). "Legal highs: staying on top of the flood of novel psychoactive substances". Therapeutic Advances in Psychopharmacology. 5 (2): 97–132. doi:10.1177/2045125314559539. PMC   4521440 . PMID   26240749.
  10. "The Misuse of Drugs Act 1971 (Amendment) Order 2017". Legislation.gov.uk.
  11. "Administrative Code 18VAC110-20-322. Placement of Chemicals in Schedule I." Virginia Law.