View source for 5F-ADB

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| IUPAC_name = Methyl (''S'')-2-[1-(5-fluoropentyl)-1''H''-indazole-3-carboxamido]-3,3-dimethylbutanoate
| image = 5F-ADB_structure.png
<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_BR = F2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_CA = Schedule II
| legal_DE = Anlage II
| legal_UK = Class B
| legal_US = Schedule I
| routes_of_administration =
<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
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<!--Identifiers-->
| CAS_number =1715016-75-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FD7BD1M9FY
| UNII2 = UN52BPP7RB
| UNII2_Ref = ([[racemate]])
| ATC_prefix =
| ATC_suffix =
| PubChem = 101895417
| KEGG = C22801
| smiles = FCCCCC[N]2C1=CC=CC=C1C(=N2)C(=O)N[C@H](C(=O)OC)C(C)(C)C
| ChemSpiderID      = 32741709
| StdInChI          = 1S/C20H28FN3O3/c1-20(2,3)17(19(26)27-4)22-18(25)16-14-10-6-7-11-15(14)24(23-16)13-9-5-8-12-21/h6-7,10-11,17H,5,8-9,12-13H2,1-4H3,(H,22,25)/t17-/m1/s1
| StdInChIKey       = PWEKNGSNNAKWBL-QGZVFWFLSA-N
<!--Chemical data-->
|  C=20|H=28|F=1|N=3|O=3
}}
'''5F-ADB''' (also known as '''MDMB-5F-PINACA'''<ref>{{cite journal | vauthors = Pulver B, Fischmann S, Gallegos A, Christie R | title = EMCDDA framework and practical guidance for naming synthetic cannabinoids | journal = Drug Testing and Analysis | volume = 15 | issue = 3 | pages = 255–276 | date = March 2023 | pmid = 36346325 | doi = 10.1002/dta.3403 }}</ref> and '''5F-MDMB-PINACA''') is an [[indazole]]-based synthetic [[cannabinoid]] from the indazole-3-carboxamide family, which has been used as an active ingredient in [[synthetic cannabis]] products and has been sold online as a [[designer drug]].<ref name="Shevyrin_2015">{{cite journal | vauthors = Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT | title = Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group | journal = Analytical and Bioanalytical Chemistry | volume = 407 | issue = 21 | pages = 6301–6315 | date = August 2015 | pmid = 25893797 | doi = 10.1007/s00216-015-8612-7 | s2cid = 31838655 }}</ref><ref>{{cite journal | vauthors = Giorgetti A, Brunetti P, Pelotti S, Auwärter V | title = Detection of AP-237 and synthetic cannabinoids on an infused letter sent to a German prisoner | journal = Drug Testing and Analysis | volume = 14 | issue = 10 | pages = 1779–1784 | date = October 2022 | pmid = 35918775 | pmc = 9804899 | doi = 10.1002/dta.3351 | s2cid = 251281159 | doi-access = free }}</ref> 5F-ADB is a potent [[agonist]] of the [[CB1 receptor|CB<sub>1</sub> receptor]],<ref>{{cite journal | vauthors = Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, Mack JB, Glass M, McGregor IS, Connor M, Kassiou M | title = Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues | journal = ACS Chemical Neuroscience | volume = 7 | issue = 9 | pages = 1241–1254 | date = September 2016 | pmid = 27421060 | doi = 10.1021/acschemneuro.6b00137 }}</ref> though it is unclear whether it is selective for this target. 5F-ADB was first identified in November 2014 from [[post-mortem]] samples taken from an individual who had died after using a product containing this substance. Subsequent testing identified 5F-ADB to have been present in a total of ten people who had died from unexplained drug overdoses in Japan between September 2014 and December 2014. 5F-ADB is believed to be extremely potent based on the very low levels detected in tissue samples, and appears to be significantly more toxic than earlier synthetic cannabinoid drugs that had previously been sold.<ref>{{cite journal | vauthors = asegawa K, Wurita A, Minakata K, Gonmori K, Yamagishi I, Nozawa H, Watanabe K, Suzuki O | title = Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products| journal = Forensic Toxicology| year = 2014 | volume=33| pages=112–121| s2cid = 45508189 | doi = 10.1007/s11419-014-0259-0 }}</ref>
In 2018, 5F-ADB was the most common synthetic cannabinoid to be identified in [[Drug Enforcement Administration]] seizures.<ref>{{cite web | url = https://ndews.umd.edu/sites/ndews.umd.edu/files/Emerging-Threat-Report-2018-Annual.pdf | title = Emerging Threat Report: Annual 2018 | publisher = Special Testing and Research Laboratory, Drug Enforcement Administration | access-date = 2019-08-01 | archive-date = 2019-08-01 | archive-url = https://web.archive.org/web/20190801190403/https://ndews.umd.edu/sites/ndews.umd.edu/files/Emerging-Threat-Report-2018-Annual.pdf | url-status = dead }}</ref>  5F-ADB was also identified in [[cannabidiol]] (CBD) products from a US-based CBD manufacturer in 2018.<ref>{{cite journal | vauthors = Poklis JL, Mulder HA, Peace MR | title = The unexpected identification of the cannabimimetic, 5F-ADB, and dextromethorphan in commercially available cannabidiol e-liquids | journal = Forensic Science International | volume = 294 | pages = e25–e27 | date = January 2019 | pmid = 30442388 | pmc = 6321772 | doi = 10.1016/j.forsciint.2018.10.019 }}</ref>
==Deaths==
5F-MDMB-PINACA has been associated with 25 deaths in Europe between 2015 and 2017.<ref>{{cite report |title=5F-MDMB-PINACA |author1=European Monitoring Centre for Drugs and Drug Addiction |author1-link=European Monitoring Centre for Drugs and Drug Addiction |author2=Europol |year=2017 |author2-link=Europol |publisher=Publications Office of the European Union |publication-place=Luxembourg |url=https://www.emcdda.europa.eu/system/files/publications/5483/2017.4963_TDAS17003ENN_PDFWEB.pdf |doi=10.2810/210307}}</ref>
==Legal status==
In the United States, 5F-ADB is a [[Controlled_Substances_Act#Schedule_I_controlled_substances|schedule I controlled substance]].<ref>{{cite web | url = https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr1221.htm | title = Schedules of Controlled Substances: Temporary Placement of Six Synthetic Cannabinoids (5F-ADB, 5F-AMB, 5F-APINACA, ADB-FUBINACA, MDMB-CHMICA and MDMB-FUBINACA) Into Schedule I | publisher = [[Drug Enforcement Administration]] | access-date = 2017-03-17 | archive-date = 2019-10-17 | archive-url = https://web.archive.org/web/20191017101101/https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr1221.htm | url-status = dead }}</ref>
5F-ADB was added to the Japanese banned drug list in December 2014.
== See also ==
{{colbegin}}
* [[5F-AB-PINACA]]
* [[5F-AMB]]
* [[5F-APINACA]]
* [[AB-CHMINACA]]
* [[AB-FUBINACA]]
* [[AB-CHFUPYCA]]
* [[AB-PINACA]]
* [[ADB-BINACA]]
* [[ADB-CHMINACA]]
* [[ADB-FUBINACA]]
* [[ADB-PINACA]]
* [[ADBICA]]
* [[APICA (synthetic cannabinoid drug)|APICA]]
* [[APINACA]]
* [[MDMB-CHMICA]]
* [[MDMB-FUBINACA]]
* [[PX-3]]
{{colend}}
== References ==
{{Reflist}}
{{Cannabinoids}}
[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Organofluorides]]
[[Category:Indazolecarboxamides]]
[[Category:Tert-butyl compounds]]