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'''Flualprazolam''' is a [[tranquilizer]] of the [[triazolobenzodiazepine]] (TBZD) class, which are [[benzodiazepine]]s (BZDs) fused with a [[triazole]] ring. It was first synthesised in 1976,<ref>{{cite patent | inventor = Hester JB, et al. | title = 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines. | url = https://patents.google.com/patent/US3987052A | country = US | number = 3987052 }}</ref> but was never marketed. It has subsequently been sold as a [[designer drug]],<ref>{{cite journal | vauthors = Wagmann L, Manier SK, Bambauer TP, Felske C, Eckstein N, Flockerzi V, Meyer MR | title = Toxicokinetics and analytical toxicology of flualprazolam: metabolic fate, isozyme mapping, human plasma concentration, and main urinary excretion products | journal = Journal of Analytical Toxicology | date = February 2020 | volume = 44 | issue = 6 | pages = 549–558 | pmid = 32104896 | doi = 10.1093/jat/bkaa019 }}</ref><ref>{{cite journal|first1=Donna M.|last1=Papsun|first2=Alex J.|last2=Krotulski|first3=Joe|last3=Homan|first4=Keith D. H.|last4=Temporal|title=Flualprazolam Blood Concentrations in 197 Forensic Investigation Cases|journal=Journal of Analytical Toxicology|doi=10.1093/jat/bkaa070|pmid=32542312|first5=Barry K.|last5=Logan|date=June 2020|volume=45 |issue=3 |pages=226–232 }}</ref><ref>{{cite journal|first1=Kathleen|last1=Rice|first2=Laura|last2=Hikin|first3=Alexander|last3=Lawson|first4=Paul R.|last4=Smith|title=Quantification of Flualprazolam in Blood by LC–MS-MS: A Case Series of Nine Deaths|journal=Journal of Analytical Toxicology|doi=10.1093/jat/bkaa098|pmid=32780842|first5=Stephen|last5=Morley|date=August 2020|volume=45 |issue=4 |pages=410–416 }}</ref> first being definitively identified as such in Sweden in 2018.<ref>[https://snpf.org/wp-content/uploads/2018/06/snpf_3_18.pdf Svenska Narkotika Polisföreningens Tidskrift, June 1 2018]</ref><ref>{{cite journal | vauthors = Kriikku P, Rasanen I, Ojanperä I, Thelander G, Kronstrand R, Vikingsson S | title = Femoral blood concentrations of flualprazolam in 33 postmortem cases | journal = Forensic Science International | volume = 307 | pages = 110101 | date = February 2020 | pmid = 31865266 | doi = 10.1016/j.forsciint.2019.110101 | hdl = 10138/323513 | s2cid = 209448865 | hdl-access = free }}</ref> It can be described as the 2'-[[fluorine|fluoro]] derivative of [[alprazolam]], the fluoro instead of chloro analogue of [[triazolam]], or the triazole analogue of [[flurazepam]], and has similar [[sedative]] and [[anxiolytic]] effects.<ref>{{cite journal | vauthors = Waters L, Manchester KR, Maskell PD, Haegeman C, Haider S | title = The use of a quantitative structure-activity relationship (QSAR) model to predict GABA-A receptor binding of newly emerging benzodiazepines | journal = Science & Justice | volume = 58 | issue = 3 | pages = 219–225 | date = May 2018 | pmid = 29685303 | doi = 10.1016/j.scijus.2017.12.004 | url = http://eprints.hud.ac.uk/id/eprint/34383/1/waters.et.al.pdf }}</ref><ref>{{cite journal | vauthors = Zawilska JB, Wojcieszak J | title = An expanding world of new psychoactive substances-designer benzodiazepines | journal = Neurotoxicology | volume = 73 | pages = 8–16 | date = July 2019 | pmid = 30802466 | doi = 10.1016/j.neuro.2019.02.015 | s2cid = 73461430 }}</ref><ref>{{cite journal | vauthors = Moosmann B, Auwärter V | title = Designer Benzodiazepines: Another Class of New Psychoactive Substances | journal = Handbook of Experimental Pharmacology | volume = 252 | pages = 383–410 | date = October 2018 | pmid = 30367253 | doi = 10.1007/164_2018_154 | publisher = Springer International Publishing | isbn = 978-3-030-10561-7 }}</ref><ref>{{cite journal| vauthors = Chetraru E, Ameline A, Gheddar L, Raul JS, Kintz P |title=Les "designer benzodiazepines" : qu'en sait-on aujourd'hui ?|journal=Toxicologie Analytique et Clinique|date=February 2018|issn=2352-0078|pages=5–18|volume=30|issue=1|doi=10.1016/j.toxac.2017.12.001|first5=Pascal|last5=Kintz}}</ref><ref>{{cite journal | vauthors = Mei V, Concheiro M, Pardi J, Cooper G | title = Validation of an LC-MS/MS Method for the Quantification of 13 Designer Benzodiazepines in Blood | journal = Journal of Analytical Toxicology | volume = 43 | issue = 9 | pages = 688–695 | date = October 2019 | pmid = 31436813 | doi = 10.1093/jat/bkz063 }}</ref>
'''Flualprazolam''' is a [[tranquilizer]] of the [[triazolobenzodiazepine]] (TBZD) class, which are [[benzodiazepine]]s (BZDs) fused with a [[triazole]] ring. It was first synthesised in 1976,<ref>{{cite patent | inventor = Hester JB, et al. | title = 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines. | url = https://patents.google.com/patent/US3987052A | country = US | number = 3987052 }}</ref> but was never marketed. It has subsequently been sold as a [[designer drug]],<ref>{{cite journal | vauthors = Wagmann L, Manier SK, Bambauer TP, Felske C, Eckstein N, Flockerzi V, Meyer MR | title = Toxicokinetics and analytical toxicology of flualprazolam: metabolic fate, isozyme mapping, human plasma concentration, and main urinary excretion products | journal = Journal of Analytical Toxicology | date = February 2020 | volume = 44 | issue = 6 | pages = 549–558 | pmid = 32104896 | doi = 10.1093/jat/bkaa019 }}</ref><ref>{{cite journal|first1=Donna M.|last1=Papsun|first2=Alex J.|last2=Krotulski|first3=Joe|last3=Homan|first4=Keith D. H.|last4=Temporal|title=Flualprazolam Blood Concentrations in 197 Forensic Investigation Cases|journal=Journal of Analytical Toxicology|doi=10.1093/jat/bkaa070|pmid=32542312|first5=Barry K.|last5=Logan|date=June 2020|volume=45 |issue=3 |pages=226–232 }}</ref><ref>{{cite journal|first1=Kathleen|last1=Rice|first2=Laura|last2=Hikin|first3=Alexander|last3=Lawson|first4=Paul R.|last4=Smith|title=Quantification of Flualprazolam in Blood by LC–MS-MS: A Case Series of Nine Deaths|journal=Journal of Analytical Toxicology|doi=10.1093/jat/bkaa098|pmid=32780842|first5=Stephen|last5=Morley|date=August 2020|volume=45 |issue=4 |pages=410–416 }}</ref><ref>{{cite journal|first1=Jiang|last1=Ling|first2=Wenqi|last2=Zhang|first3=Xiaojun|last3=Yan|first4=Wenlong|last4=Liu|title=Sensitive detection and primary metabolism analysis of flualprazolam in blood|journal=Journal of Forensic and Legal Medicine|date=August 2022|issn=1752-928X|pages=102388|volume=90|doi=10.1016/j.jflm.2022.102388|pmid=35691207|first5=Yanyan|last5=Wang|first6=Yanjun|last6=Ding}}</ref> first being definitively identified as such in Sweden in 2018.<ref>[https://snpf.org/wp-content/uploads/2018/06/snpf_3_18.pdf Svenska Narkotika Polisföreningens Tidskrift, June 1 2018]</ref><ref>{{cite journal | vauthors = Kriikku P, Rasanen I, Ojanperä I, Thelander G, Kronstrand R, Vikingsson S | title = Femoral blood concentrations of flualprazolam in 33 postmortem cases | journal = Forensic Science International | volume = 307 | pages = 110101 | date = February 2020 | pmid = 31865266 | doi = 10.1016/j.forsciint.2019.110101 | hdl = 10138/323513 | s2cid = 209448865 | hdl-access = free }}</ref> It can be described as the 2'-[[fluorine|fluoro]] derivative of [[alprazolam]], the fluoro instead of chloro analogue of [[triazolam]], or the triazole analogue of [[flurazepam]], and has similar [[sedative]] and [[anxiolytic]] effects.<ref>{{cite journal | vauthors = Waters L, Manchester KR, Maskell PD, Haegeman C, Haider S | title = The use of a quantitative structure-activity relationship (QSAR) model to predict GABA-A receptor binding of newly emerging benzodiazepines | journal = Science & Justice | volume = 58 | issue = 3 | pages = 219–225 | date = May 2018 | pmid = 29685303 | doi = 10.1016/j.scijus.2017.12.004 | url = http://eprints.hud.ac.uk/id/eprint/34383/1/waters.et.al.pdf }}</ref><ref>{{cite journal | vauthors = Zawilska JB, Wojcieszak J | title = An expanding world of new psychoactive substances-designer benzodiazepines | journal = Neurotoxicology | volume = 73 | pages = 8–16 | date = July 2019 | pmid = 30802466 | doi = 10.1016/j.neuro.2019.02.015 | s2cid = 73461430 }}</ref><ref>{{cite journal | vauthors = Moosmann B, Auwärter V | title = Designer Benzodiazepines: Another Class of New Psychoactive Substances | journal = Handbook of Experimental Pharmacology | volume = 252 | pages = 383–410 | date = October 2018 | pmid = 30367253 | doi = 10.1007/164_2018_154 | publisher = Springer International Publishing | isbn = 978-3-030-10561-7 }}</ref><ref>{{cite journal| vauthors = Chetraru E, Ameline A, Gheddar L, Raul JS, Kintz P |title=Les "designer benzodiazepines" : qu'en sait-on aujourd'hui ?|journal=Toxicologie Analytique et Clinique|date=February 2018|issn=2352-0078|pages=5–18|volume=30|issue=1|doi=10.1016/j.toxac.2017.12.001|first5=Pascal|last5=Kintz}}</ref><ref>{{cite journal | vauthors = Mei V, Concheiro M, Pardi J, Cooper G | title = Validation of an LC-MS/MS Method for the Quantification of 13 Designer Benzodiazepines in Blood | journal = Journal of Analytical Toxicology | volume = 43 | issue = 9 | pages = 688–695 | date = October 2019 | pmid = 31436813 | doi = 10.1093/jat/bkz063 }}</ref>


== Legal status ==
== Legal status ==

Revision as of 18:41, 13 June 2022

Flualprazolam
Legal status
Legal status
Identifiers
  • 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC17H12ClFN4
Molar mass326.76 g·mol−1
3D model (JSmol)
  • CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4F
  • 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,9H2,1H3
  • Key: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 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, the fluoro instead of chloro analogue of triazolam, or the triazole analogue of flurazepam, and has similar sedative and anxiolytic effects.[9][10][11][12][13]

Legal status

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]

See also

References

  1. ^ https://www.oregon.gov/pharmacy/Documents/Permanently_Adopted_TrackedChanges_Div_041_Div_080_BP_8-2020.pdf [bare URL PDF]
  2. ^ US 3987052, Hester JB, et al., "6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines." 
  3. ^ Wagmann L, Manier SK, Bambauer TP, Felske C, Eckstein N, Flockerzi V, Meyer MR (February 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, Donna M.; Krotulski, Alex J.; Homan, Joe; Temporal, Keith D. H.; Logan, Barry K. (June 2020). "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, Kathleen; Hikin, Laura; Lawson, Alexander; Smith, Paul R.; Morley, Stephen (August 2020). "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, Jiang; Zhang, Wenqi; Yan, Xiaojun; Liu, Wenlong; Wang, Yanyan; Ding, Yanjun (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. ISSN 1752-928X. PMID 35691207.
  7. ^ Svenska Narkotika Polisföreningens Tidskrift, June 1 2018
  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". Handbook of Experimental Pharmacology. 252. Springer International Publishing: 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.
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