5F-APINACA

{{Short description|Chemical compound}}

{{distinguish|5F-AB-PINACA}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| IUPAC_name = N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide

| image = 5F-APINACA.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_BR = F2

| legal_BR_comment = {{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}}

| legal_CA = Schedule II

| legal_UK = Class B

| legal_US = Schedule I

| legal_DE = Anlage II

| legal_UN = P II

| legal_UN_comment = {{Cite web |title=Substance Details 5F-APINACA |url=https://www.unodc.org/LSS/Substance/Details/6335a860-435e-4182-933b-dec8d6490418 |access-date=2024-01-22}}

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 1400742-13-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TX64ZY5P0R

| ATC_prefix =

| ATC_suffix =

| PubChem = 71711119

| KEGG = C22695

| ChemSpiderID = 29339965

| smiles = O=C(NC1(C[C@@H]2C3)C[C@H](C2)C[C@H]3C1)C4=NN(CCCCCF)C5=CC=CC=C54

| StdInChI = 1S/C23H30FN3O/c24-8-4-1-5-9-27-20-7-3-2-6-19(20)21(26-27)22(28)25-23-13-16-10-17(14-23)12-18(11-16)15-23/h2-3,6-7,16-18H,1,4-5,8-15H2,(H,25,28)/t16-,17+,18-,23?

| StdInChIKey = UCMFSGVIEPXYIV-XHICYHHKSA-N

| synonyms = 5F-AKB-48, 5F-AKB48

| C=23 | H=30 | F=1 | N=3 | O=1

}}

5F-APINACA (also known as A-5F-PINACA,{{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 }} 5F-AKB-48 or 5F-AKB48) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/12065 | title=AKB48 N-(5-fluoropentyl) analog | publisher=Cayman Chemical | access-date=6 July 2015}}{{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 | access-date=6 July 2015}} 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.[http://patentscope.wipo.int/search/en/detail.jsf?docId=WO2003035005 WO 2003/035005]

5F-APINACA was first identified in South Korea.{{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 | journal=Forensic Toxicology |date=January 2014 | volume=32 | issue=1 | pages=82–88 | doi=10.1007/s11419-013-0213-6| s2cid=23058813 }} It is expected to be a potent agonist of the CB₁ receptor and CB₂ receptor.{{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 | access-date=6 July 2015}} Its metabolism has been described in literature.{{cite journal | title=Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry | vauthors = Jang M, Shin I, Kim J, Yang W | journal=Forensic Toxicology |date=February 2015 | doi=10.1007/s11419-015-0265-x | volume=33 |issue = 2| pages=221–234| s2cid=3038555 }}{{cite journal | vauthors = 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 | journal = Forensic Science International | volume = 246 | pages = 98–103 | date = January 2015 | pmid = 25485949 | doi = 10.1016/j.forsciint.2014.11.012 }}{{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 | journal = Drug Testing and Analysis | volume = 7 | issue = 3 | pages = 199–206 | date = March 2015 | pmid = 24802286 | doi = 10.1002/dta.1663 }}{{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 | journal = The AAPS Journal | volume = 17 | issue = 3 | pages = 660–677 | date = May 2015 | pmid = 25721194 | pmc = 4406957 | doi = 10.1208/s12248-015-9721-0 }}