Chemistry:5F-APINACA
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| Other names | 5F-AKB-48, 5F-AKB48 |
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| Formula | C23H30FN3O |
| Molar mass | 383.511 g·mol−1 |
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5F-APINACA (also known as A-5F-PINACA,[2] 5F-AKB-48 or 5F-AKB48) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.[3][4] 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.[5]
5F-APINACA was first identified in South Korea.[6] It is expected to be a potent agonist of the CB1 receptor and CB2 receptor.[7] Its metabolism has been described in literature.[8][9][10][11]
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.[12]
Legality
In the United States, 5F-APINACA is a Schedule I controlled substance.[13]
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.[14]
5F-APINACA is banned in the Czech Republic.[15]
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
- ↑ "Substance Details 5F-APINACA". https://www.unodc.org/LSS/Substance/Details/6335a860-435e-4182-933b-dec8d6490418.
- ↑ Pulver, Benedikt; Fischmann, Svenja; Gallegos, Ana; Christie, Rachel (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis 15 (3): 255–276. doi:10.1002/dta.3403.
- ↑ "AKB48 N-(5-fluoropentyl) analog". Cayman Chemical. https://www.caymanchem.com/app/template/Product.vm/catalog/12065.
- ↑ "5F-AKB48". Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG). 18 February 2013. http://www.swgdrug.org/Monographs/5F-AKB48.pdf.
- ↑ WO 2003/035005
- ↑ "Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013". Forensic Toxicology 32 (1): 82–88. January 2014. doi:10.1007/s11419-013-0213-6.
- ↑ "AKB48 (APINACA) and 5F-AKB48 (5F-APINACA)". Drug Enforcement Administration. May 2013. http://deadiversion.usdoj.gov/drug_chem_info/spice/akb48.pdf.
- ↑ "Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry". Forensic Toxicology 33 (2): 221–234. February 2015. doi:10.1007/s11419-015-0265-x.
- ↑ "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. doi:10.1016/j.forsciint.2014.11.012. PMID 25485949. http://www.fsijournal.org/article/S0379-0738%2814%2900477-0/abstract.
- ↑ "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. doi:10.1002/dta.1663. PMID 24802286.
- ↑ "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): 660–77. May 2015. doi:10.1208/s12248-015-9721-0. PMID 25721194.
- ↑ "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology 34 (2): 329–343. 1 July 2016. doi:10.1007/s11419-016-0320-2. PMID 27429655.
- ↑ "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. https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr1221.htm.
- ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.
- ↑ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (in Czech). Ministerstvo zdravotnictví. http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf.
External links
- "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. doi:10.1007/s13181-016-0571-7. PMID 27456262.
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