flubromazolam

{{Short description|Triazolobenzodiazepine drug}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid =

| IUPAC_name = 8-bromo-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a] [1,4]benzodiazepine

| image = Flubromazolam.svg

| image_class = skin-invert-image

| width = 200

| tradename =

| legal_BR = B1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule IV

| legal_DE = Anlage II

| legal_UK = PSA

| legal_US = Schedule I

| legal_US_comment =

| legal_status = Illegal in Sweden and Switzerland

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 612526-40-6

| PubChem = 21930924

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 10684757

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 1BF1HN5GWD

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C22817

| C = 17

| H = 12

| Br = 1

| F = 1

| N = 4

| molecular_weight =

| smiles = BrC1=CC3=C(C=C1)[N]2C(=NN=C2C)CN=C3C4=C(C=CC=C4)F

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C17H12BrFN4/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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = VXGSZBZQCBNUIP-UHFFFAOYSA-N

}}

Flubromazolam (JYI-73) Cook JM, et al. Stereospecific anxiolytic and anticonvulsant agents with reduced muscle-relaxant, sedative-hypnotic and ataxic effects. [https://patents.google.com/patent/US7618958B2 US7618958]{{cite web | url=https://patents.google.com/patent/EP0072029B1 | title=Patent EP 0072029 B1 - Triazolobenzazepines, process and intermediates for their preparation and medicines containing them | date=22 October 1986 | access-date=6 August 2015 | vauthors = Borer R, Gerecke M, Kyburz E }}{{cite journal | vauthors = Hester JB, Rudzik AD, Kamdar BV | title = 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines which have central nervous system depressant activity | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 11 | pages = 1078–81 | date = November 1971 | pmid = 5165540 | doi = 10.1021/jm00293a015 }} is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives.{{cite web | url= https://www.caymanchem.com/product/16435 | title=Flubromazolam | publisher=Cayman Chemical | access-date=20 November 2015}}{{cite journal | vauthors = Huppertz LM, Bisel P, Westphal F, Franz F, Auwärter V, Moosmann B | title=Characterization of the four designer benzodiazepines clonazolam, deschloroetizolam, flubromazolam, and meclonazepam, and identification of their in vitro metabolites | date=July 2015 | journal=Forensic Toxicology | volume=33 | issue=2 | pages=388–395 | doi=10.1007/s11419-015-0277-6| s2cid=33278305 }}{{cite journal | vauthors = Chaslot M, El Balkhi S, Robin T, Morichon J, Picard N, Saint-Marcoux F | title=Exploration des métabolites de 8 benzodiazépines de synthèse | journal=Toxicologie Analytique et Clinique | date=June 2016 | volume=28 | issue=2 | pages=S32 | doi=10.1016/j.toxac.2016.03.053}}{{cite journal | vauthors = Pettersson Bergstrand M, Helander A, Hansson T, Beck O | title = Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays | journal = Drug Testing and Analysis | volume = 9 | issue = 4 | pages = 640–645 | date = April 2017 | pmid = 27366870 | doi = 10.1002/dta.2003 }}{{cite journal | vauthors = Høiseth G, Tuv SS, Karinen R | title = Blood concentrations of new designer benzodiazepines in forensic cases | journal = Forensic Science International | volume = 268 | pages = 35–38 | date = November 2016 | pmid = 27685473 | doi = 10.1016/j.forsciint.2016.09.006 }}{{cite journal | vauthors = Manchester KR, Maskell PD, Waters L | title = Experimental versus theoretical log D_7.4, pK_a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances | journal = Drug Testing and Analysis | volume = 10 | issue = 8 | pages = 1258–1269 | date = March 2018 | pmid = 29582576 | doi = 10.1002/dta.2387 | s2cid = 31098917 | url = https://pure.hud.ac.uk/ws/files/13273614/logDpKaPPB_13thMar2018.pdf }}{{cite journal | vauthors = Wohlfarth A, Vikingsson S, Roman M, Andersson M, Kugelberg FC, Green H, Kronstrand R | title = Looking at flubromazolam metabolism from four different angles: Metabolite profiling in human liver microsomes, human hepatocytes, mice and authentic human urine samples with liquid chromatography high-resolution mass spectrometry | journal = Forensic Science International | volume = 274 | pages = 55–63 | date = May 2017 | pmid = 27863836 | doi = 10.1016/j.forsciint.2016.10.021 | series = Special Issue on the 54th Annual Meeting of the International Association of Forensic Toxicologists (TIAFT) Brisbane from August 28 to September 1, 2016 }} 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.{{cite journal | vauthors = Moosmann B, King LA, Auwärter V | title = Designer benzodiazepines: A new challenge | journal = World Psychiatry | volume = 14 | issue = 2 | pages = 248 | date = June 2015 | pmid = 26043347 | pmc = 4471986 | doi = 10.1002/wps.20236 }}{{cite journal | vauthors = Huppertz LM, Moosmann B, Auwärter V | title = Flubromazolam - Basic pharmacokinetic evaluation of a highly potent designer benzodiazepine | journal = Drug Testing and Analysis | volume = 10 | issue = 1 | pages = 206–211 | date = January 2018 | pmid = 28378533 | doi = 10.1002/dta.2203 }} Life-threatening adverse reactions have been observed at doses of only 3 mg of flubromazolam.{{cite journal | vauthors = Łukasik-Głębocka M, Sommerfeld K, Teżyk A, Zielińska-Psuja B, Panieński P, Żaba C | title = Flubromazolam--A new life-threatening designer benzodiazepine | journal = Clinical Toxicology | volume = 54 | issue = 1 | pages = 66–8 | date = 2016 | pmid = 26585557 | doi = 10.3109/15563650.2015.1112907 | s2cid = 4114360 }}