5F-APINACA explained

5F-APINACA should not be confused with 5F-AB-PINACA.

5F-APINACA (also known as A-5F-PINACA,^[1] 5F-AKB-48 or 5F-AKB48) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.^{[2] [3]} 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.^[4]

5F-APINACA was first identified in South Korea.^[5] It is expected to be a potent agonist of the CB₁ receptor and CB₂ receptor.^[6] Its metabolism has been described in literature.^{[7] [8] [9] [10]}

Pharmacology

5F-APINACA acts as a full agonist with a binding affinity of 1.94 nM at CB₁ and 0.266 nM at CB₂ cannabinoid receptors.^[11]

Legality

In the United States, 5F-APINACA is a Schedule I controlled substance.^[12]

5F-APINACA is an Anlage II controlled drug in Germany since July 2013.

As of October 2015, 5F-APINACA is a controlled substance in China.^[13]

5F-APINACA is banned in the Czech Republic.^[14]

See also

• 5F-ADB
• 5F-AMB
• AB-FUBINACA
• AB-CHFUPYCA
• AB-PINACA
• ADB-CHMINACA
• ADB-FUBINACA
• ADB-PINACA
• ADBICA
• APICA
• APINACA
• FUB-APINACA
• MDMB-CHMICA
• PX-3

External links

• Abouchedid R, Ho JH, Hudson S, Dines A, Archer JR, Wood DM, Dargan PI . Acute Toxicity Associated with Use of 5F-Derivations of Synthetic Cannabinoid Receptor Agonists with Analytical Confirmation . Journal of Medical Toxicology . 12 . 4 . 396–401 . December 2016 . 27456262 . 5135680 . 10.1007/s13181-016-0571-7 .

Notes and References

1. Pulver B, Fischmann S, Gallegos A, Christie R . EMCDDA framework and practical guidance for naming synthetic cannabinoids . Drug Testing and Analysis . 15 . 3 . 255–276 . March 2023 . 36346325 . 10.1002/dta.3403 .
2. Web site: AKB48 N-(5-fluoropentyl) analog . Cayman Chemical . 6 July 2015.
3. Web site: 5F-AKB48 . Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG) . 18 February 2013 . 6 July 2015.
4. http://patentscope.wipo.int/search/en/detail.jsf?docId=WO2003035005 WO 2003/035005
5. Chung H, Choi H, Heo S, Kim E, Lee J . Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013 . Forensic Toxicology . January 2014 . 32 . 1 . 82–88 . 10.1007/s11419-013-0213-6. 23058813 .
6. Web site: AKB48 (APINACA) and 5F-AKB48 (5F-APINACA) . Drug Enforcement Administration . May 2013 . 6 July 2015.
7. Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry . Jang M, Shin I, Kim J, Yang W . Forensic Toxicology . February 2015 . 10.1007/s11419-015-0265-x . 33 . 2. 221–234. 3038555 .
8. Karinen R, Tuv SS, Øiestad EL, Vindenes V . 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 . Forensic Science International . 246 . 98–103 . January 2015 . 25485949 . 10.1016/j.forsciint.2014.11.012 .
9. Holm NB, Pedersen AJ, Dalsgaard PW, Linnet K . 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 . Drug Testing and Analysis . 7 . 3 . 199–206 . March 2015 . 24802286 . 10.1002/dta.1663 .
10. Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, Huestis MA . Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA . The AAPS Journal . 17 . 3 . 660–677 . May 2015 . 25721194 . 4406957 . 10.1208/s12248-015-9721-0 .
11. Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE . Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice . Forensic Toxicology . 34 . 2 . 329–343 . 1 July 2016 . 27429655 . 4929166 . 10.1007/s11419-016-0320-2 .
12. Web site: 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 . . 2017-03-17 . 2019-10-17 . https://web.archive.org/web/20191017101101/https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr1221.htm . dead .
13. Web site: 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 . Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs" . China Food and Drug Administration . 27 September 2015 . Chinese . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . 1 October 2015 . dead .
14. Web site: Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) . Ministerstvo zdravotnictví . Czech . 2016-02-06 . 2016-03-09 . https://web.archive.org/web/20160309174659/http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf . dead .