5F-APINACA

Not to be confused with 5F-AB-PINACA.

5F-APINACA (also known as A-5F-PINACA,^[3] 5F-AKB-48 or 5F-AKB48) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.^[4][5] 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.^[6]

5F-APINACA

Clinical data
Other names	5F-AKB-48, 5F-AKB48
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I UN: Psychotropic Schedule II[2]
Identifiers
IUPAC name N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide
CAS Number	1400742-13-3
PubChem CID	71711119
ChemSpider	29339965
UNII	TX64ZY5P0R
KEGG	C22695
CompTox Dashboard (EPA)	DTXSID80856800
Chemical and physical data
Formula	C23H30FN3O
Molar mass	383.511 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(NC1(C[C@@H]2C3)C[C@H](C2)C[C@H]3C1)C4=NN(CCCCCF)C5=CC=CC=C54
InChI InChI=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? Key:UCMFSGVIEPXYIV-XHICYHHKSA-N

5F-APINACA was first identified in South Korea.^[7] It is expected to be a potent agonist of the CB₁ receptor and CB₂ receptor.^[8] Its metabolism has been described in literature.^{[9][10][11][12]}

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.^[13]

Legality

In the United States, 5F-APINACA is a Schedule I controlled substance.^[14]

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.^[15]

5F-APINACA is banned in the Czech Republic.^[16]

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

References

1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
2. "Substance Details 5F-APINACA". Retrieved 2024-01-22.
3. Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
4. "AKB48 N-(5-fluoropentyl) analog". Cayman Chemical. Retrieved 6 July 2015.
5. "5F-AKB48" (PDF). Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG). 18 February 2013. Retrieved 6 July 2015.
6. WO 2003/035005
7. Chung H, Choi H, Heo S, Kim E, Lee J (January 2014). "Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013". Forensic Toxicology. 32 (1): 82–88. doi:10.1007/s11419-013-0213-6. S2CID 23058813.
8. "AKB48 (APINACA) and 5F-AKB48 (5F-APINACA)" (PDF). Drug Enforcement Administration. May 2013. Retrieved 6 July 2015.
9. Jang M, Shin I, Kim J, Yang W (February 2015). "Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry". Forensic Toxicology. 33 (2): 221–234. doi:10.1007/s11419-015-0265-x. S2CID 3038555.
10. Karinen R, Tuv SS, Øiestad EL, Vindenes V (January 2015). "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. doi:10.1016/j.forsciint.2014.11.012. PMID 25485949.
11. Holm NB, Pedersen AJ, Dalsgaard PW, Linnet K (March 2015). "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. doi:10.1002/dta.1663. PMID 24802286.
12. Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, et al. (May 2015). "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. doi:10.1208/s12248-015-9721-0. PMC 4406957. PMID 25721194.
13. Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (1 July 2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.
14. "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". Drug Enforcement Administration. Archived from the original on 2019-10-17. Retrieved 2017-03-17.
15. "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"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
16. "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví. Archived from the original (PDF) on 2016-03-09. Retrieved 2016-02-06.

External links

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