5F-APINACA: Difference between revisions

| image = 5F-APINACA.pngsvg

| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->

'''5F-APINACA''' (also known as '''A-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> '''5F-AKB-48''' or '''5F-AKB48''') is an [[indazole]]-based [[synthetic cannabinoid]] that has been sold online as a [[designer drug]].<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/12065 | title=AKB48 ''N''-(5-fluoropentyl) analog | publisher=Cayman Chemical | accessdateaccess-date=6 July 2015}}</ref><ref>{{cite web | url=http://www.swgdrug.org/Monographs/5F-AKB48.pdf | title=5F-AKB48 | publisher=Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG) | date=18 February 2013 | accessdateaccess-date=6 July 2015}}</ref> Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropentyl chain on the indazole 1-position, and 5F-APINACA falls within the claims of this patent, as despite not being disclosed as an example, it is very similar to the corresponding [[pentanenitrile]] and 4-chlorobutyl compounds which are claimed as examples 3 and 4.<ref>[http://patentscope.wipo.int/search/en/detail.jsf?docId=WO2003035005 WO 2003/035005]</ref>

5F-APINACA was first identified in South Korea.<ref>{{cite journal | vauthors = Chung H, Choi H, Heo S, Kim E, Lee J | title=Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013 | author=Heesun Chung | author2=Hyeyoung Choi | author3=Sewoong Heo | author4=Eunmi Kim | author5=Jaesin Lee | journal=Forensic Toxicology |date=January 2014 | volume=32 | issue=1 | pages=82–88 | doi=10.1007/s11419-013-0213-6| s2cid=23058813 }}</ref> It is expected to be a potent [[agonist]] of the [[CB1 receptor|CB₁ receptor]] and [[CB2 receptor|CB₂ receptor]].<ref>{{cite web | url=http://deadiversion.usdoj.gov/drug_chem_info/spice/akb48.pdf | title=AKB48 (APINACA) and 5F-AKB48 (5F-APINACA) | publisher=Drug Enforcement Administration | date=May 2013 | accessdateaccess-date=6 July 2015}}</ref> Its metabolism has been described in literature.<ref>{{cite journal | title=Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry | authorvauthors =Moonhee Jang | author2=IlchungM, Shin | author3=JihyunI, Kim| author4=WonkyungJ, Yang W | journal=Forensic Toxicology |date=February 2015 | doi=10.1007/s11419-015-0265-x | volume=33 |issue = 2| pages=221–234| s2cid=3038555 }}</ref><ref>{{cite journal | urlvauthors =http://www.fsijournal.org/article/S0379-0738%2814%2900477-0/abstract Karinen R, Tuv SS, Øiestad EL, Vindenes V | title = Concentrations of APINACA, 5F-APINACA, UR-144 and its degradant product in blood samples from six impaired drivers compared to previous reported concentrations of other synthetic cannabinoids | authorjournal =Ritva KarinenForensic |Science author2=SiljaInternational Skogstad| Tuvvolume | author3=Elisabeth Leere246 Øiestad| author4pages =Vigdis Vindenes98–103 | journaldate =Forensic Science International |date=January 2015 | volumepmid =246 | pages=98–10325485949 | doi = 10.1016/j.forsciint.2014.11.012 | pmid=25485949}}</ref><ref>{{cite journal | vauthors = Holm NB, Pedersen AJ, Dalsgaard PW, Linnet K | title = Metabolites of 5F-AKB-48, a synthetic cannabinoid receptor agonist, identified in human urine and liver microsomal preparations using liquid chromatography high-resolution mass spectrometry | authorjournal =Niels BjerreDrug HolmTesting |and author2=Anders Just PedersenAnalysis | author3volume =Petur Weihe7 Dalsgaard| author4issue =Kristian Linnet3 | journalpages =Drug Testing and Analysis199–206 | date = March 2015 | volume=7pmid | issue=3 | pages=199–20624802286 | doi = 10.1002/dta.1663 | pmid=24802286}}</ref><ref>{{cite journal | vauthors = Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, Huestis MA | title = Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA | authorjournal =Ariane WohlfarthThe |AAPS author2=Marisol S. CastanetoJournal | author3=Mingshevolume Zhu| author4=Shaokun Pang17 | author5issue =Karl B.3 Scheidweiler| author6pages =Robert Kronstrand660–677 | author7date =Marilyn A.May Huestis2015 | journal=Thepmid AAPS Journal |date=May 2015 25721194 | volume=17pmc | issue=3 | pages=660–6774406957 | doi = 10.1208/s12248-015-9721-0 | pmid=25721194 | pmc=4406957}}</ref>

5F-APINACA acts as a [[full agonist]] with a [[Affinity (pharmacology)#Protein-ligand binding|binding affinity]] of 1.94&nbsp;nM at [[Cannabinoid receptor type 1|CB₁]] and 0.266&nbsp;nM at [[Cannabinoid receptor type 2|CB₂]] [[cannabinoid]] receptors.<ref>{{cite journal |first1=Cornelius|last1 vauthors = Hess|first2=ClaraT.|last2= C, Schoeder|first3=Thanigaimalai|last3= CT, Pillaiyar|first4=Burkhard|last4= T, Madea B, Müller CE | title = Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice | journal = Forensic Toxicology |date volume =1 July34 2016|issn issue =1860-8965 2 | pages = 329–343 |volume date =34 1 July 2016 |issue pmid =2 27429655 | pmc = 4929166 | doi = 10.1007/s11419-016-0320-2|first5=ChristaE.|last5=Müller|pmid=27429655|pmc=4929166 }}</ref>

In the United States, 5F-APINACA 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>

As of October 2015, 5F-APINACA is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | trans-title = Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs" | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdateaccess-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

5F-APINACA is banned in the Czech Republic.<ref>{{cite web | url=http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | title=Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) | publisher=Ministerstvo zdravotnictví | language=Czech | access-date=2016-02-06 | archive-date=2016-03-09 | archive-url=https://web.archive.org/web/20160309174659/http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | url-status=dead }}</ref>

== See also ==

== References ==

== External links ==

* {{cite journal | doivauthors = 10.1007/s13181-016-0571-7|Abouchedid pmidR, =Ho 27456262|JH, pmcHudson S, =Dines A, Archer JR, Wood DM, Dargan PI 5135680| title = Acute Toxicity Associated with Use of 5F-Derivations of Synthetic Cannabinoid Receptor Agonists with Analytical Confirmation | journal = Journal of Medical Toxicology | volume = 12 | issue = 4 | pages = 396–401| year = 2016| last1date = Abouchedid|December first12016 = Rachelle| last2pmid = Ho|27456262 first2 = James H.| last3pmc = Hudson| first3 =5135680 Simon| last4doi = Dines| first4 = Alison| last5 = Archer| first5 = John R10.1007/s13181-016-0571-7 H.| last6 = Wood| first6 = David M.| last7 = Dargan| first7 = Paul I.}}