Flualprazolam (original) (raw)

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Triazolobenzodiazepine drug

Flualprazolam
Legal status
Legal status AU: Unscheduled BR: Class B1 (Psychoactive drugs)[1] CA: Schedule IV DE: NpSG (Industrial and scientific use only) NZ: Unscheduled UK: Class C US: Schedule I UN: Psychotropic Schedule IV SE: Förteckning I
Identifiers
IUPAC name 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine
CAS Number 28910-91-0
PubChem CID 10359044
ChemSpider 8534493
UNII FWF5L8D2BE
KEGG C22815 checkY
CompTox Dashboard (EPA) DTXSID801132654 Edit this at Wikidata
Chemical and physical data
Formula C17H12ClFN4
Molar mass 326.76 g·mol−1
3D model (JSmol) Interactive image
SMILES CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4F
InChI InChI=1S/C17H12ClFN4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3Key:MPZVLJCMGPYWQQ-UHFFFAOYSA-N

Flualprazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It was first synthesised in 1976,[2] but was never marketed. It can be seen as the triazolo version of fludiazepam. It has subsequently been sold as a designer drug,[3][4][5][6] first being definitively identified as such in Sweden in 2018.[7][8] 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.[9][10][11][12][13]

Flualprazolam is banned in Sweden, also is illegal in the UK.[14] In December 2019, the World Health Organization recommended flualprazolam for international scheduling as a Schedule IV medication under the Convention on Psychotropic Substances.[15]

In the United States, Oregon and Virginia have placed Flualprazolam into Schedule I.[16] On December 23, 2022, the DEA announced it had begun consideration on the matter of placing Flualprazolam under temporary Schedule I status.[17] Later on July 25, 2023, the DEA published a pre-print notice that Flualprazolam would become temporarily scheduled as a Schedule I controlled substance from 26 July 2023 to 26 July 2025.[18]

  1. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  2. ^ US 3987052, Hester Jr JB, "6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines.", issued 19 October 1976, assigned to Pharmacia and Upjohn Co.
  3. ^ Wagmann L, Manier SK, Bambauer TP, Felske C, Eckstein N, Flockerzi V, Meyer MR (July 2020). "Toxicokinetics and Analytical Toxicology of Flualprazolam: Metabolic Fate, Isozyme Mapping, Human Plasma Concentration and Main Urinary Excretion Products". Journal of Analytical Toxicology. 44 (6): 549–558. doi:10.1093/jat/bkaa019. PMID 32104896.
  4. ^ Papsun DM, Krotulski AJ, Homan J, Temporal KD, Logan BK (March 2021). "Flualprazolam Blood Concentrations in 197 Forensic Investigation Cases". Journal of Analytical Toxicology. 45 (3): 226–232. doi:10.1093/jat/bkaa070. PMID 32542312.
  5. ^ Rice K, Hikin L, Lawson A, Smith PR, Morley S (April 2021). "Quantification of Flualprazolam in Blood by LC-MS-MS: A Case Series of Nine Deaths". Journal of Analytical Toxicology. 45 (4): 410–416. doi:10.1093/jat/bkaa098. PMID 32780842.
  6. ^ Ling J, Zhang W, Yan X, Liu W, Wang Y, Ding Y (August 2022). "Sensitive detection and primary metabolism analysis of flualprazolam in blood". Journal of Forensic and Legal Medicine. 90: 102388. doi:10.1016/j.jflm.2022.102388. PMID 35691207.
  7. ^ "21 nya droger förbjudna hittills I år" [21 new drugs banned so far this year] (PDF). Svenska Narkotika Polisföreningens Tidskrift [_The Journal of the Swedish Narcotics Police Association_]. June 2018. Archived from the original (PDF) on 5 August 2018. Retrieved 23 April 2023.
  8. ^ Kriikku P, Rasanen I, Ojanperä I, Thelander G, Kronstrand R, Vikingsson S (February 2020). "Femoral blood concentrations of flualprazolam in 33 postmortem cases". Forensic Science International. 307: 110101. doi:10.1016/j.forsciint.2019.110101. hdl:10138/323513. PMID 31865266. S2CID 209448865.
  9. ^ Waters L, Manchester KR, Maskell PD, Haegeman C, Haider S (May 2018). "The use of a quantitative structure-activity relationship (QSAR) model to predict GABA-A receptor binding of newly emerging benzodiazepines" (PDF). Science & Justice. 58 (3): 219–225. doi:10.1016/j.scijus.2017.12.004. PMID 29685303.
  10. ^ Zawilska JB, Wojcieszak J (July 2019). "An expanding world of new psychoactive substances-designer benzodiazepines". Neurotoxicology. 73: 8–16. doi:10.1016/j.neuro.2019.02.015. PMID 30802466. S2CID 73461430.
  11. ^ Moosmann B, Auwärter V (October 2018). "Designer Benzodiazepines: Another Class of New Psychoactive Substances". New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. Springer International Publishing. pp. 383–410. doi:10.1007/164_2018_154. ISBN 978-3-030-10561-7. PMID 30367253.
  12. ^ Chetraru E, Ameline A, Gheddar L, Raul JS, Kintz P (February 2018). "Les "designer benzodiazepines" : qu'en sait-on aujourd'hui ?". Toxicologie Analytique et Clinique. 30 (1): 5–18. doi:10.1016/j.toxac.2017.12.001. ISSN 2352-0078.
  13. ^ Mei V, Concheiro M, Pardi J, Cooper G (October 2019). "Validation of an LC-MS/MS Method for the Quantification of 13 Designer Benzodiazepines in Blood". Journal of Analytical Toxicology. 43 (9): 688–695. doi:10.1093/jat/bkz063. PMID 31436813.
  14. ^ Riksdagsförvaltningen. "Förordning (1992:1554) om kontroll av narkotika". riksdagen.se (in Swedish).
  15. ^ "News: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". www.unodc.org.
  16. ^ "Permanently Adopted Tracked Changes" (PDF). Retrieved 23 April 2023.
  17. ^ "(Proposed Rule) Schedules of Controlled Substances: Temporary Placement of Etizolam, Flualprazolam, Clonazolam, Flubromazolam, and Diclazepam in Schedule I". Federal Register. DEA. 23 December 2022.
  18. ^ "Schedules of Controlled Substances: Temporary Placement of Etizolam, Flualprazolam, Clonazolam, Flubromazolam, and Diclazepam in Schedule I" (PDF). Federal Register. DEA. 25 July 2023. Retrieved 25 July 2023.