5F-APINACA

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

Not to be confused with 5F-AB-PINACA.
5F-APINACA
Clinical data
Other names5F-AKB-48, 5F-AKB48
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30FN3O
Molar mass383.511 g·mol−1
3D model (JSmol)

5F-APINACA was first identified in South Korea.[4] It is expected to be a potent agonist of the CB1 receptor and CB2 receptor.[5] Its metabolism has been described in literature.[6][7][8][9]

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.[10]

Legality

In the United States, 5F-APINACA is a Schedule I controlled substance.[11]

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.[12]

5F-APINACA is banned in the Czech Republic.[13]

gollark: What do they actually *do*, though?
gollark: Can you be more specific? IIRC Star Trek phasers did a gazillion random things depending on plot convenience.
gollark: I'm hoping there's some comparatively cheap way to at least mitigate the climatic issues, because otherwise it seems unlikely that (without massive societal change of some kind) much will be done.
gollark: In practice I think the fuel is unlikely to run out, given the multitude of ways to increase uranium use efficiency which aren't economical right now.
gollark: Really? The statistics I vaguely remember reading said we had something like 50 years even using it inefficiently.

See also

References
  1. "AKB48 N-(5-fluoropentyl) analog". Cayman Chemical. Retrieved 6 July 2015.
  2. "5F-AKB48" (PDF). Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG). 18 February 2013. Retrieved 6 July 2015.
  3. WO 2003/035005
  4. Heesun Chung; Hyeyoung Choi; Sewoong Heo; Eunmi Kim; Jaesin Lee (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.
  5. "AKB48 (APINACA) and 5F-AKB48 (5F-APINACA)" (PDF). Drug Enforcement Administration. May 2013. Retrieved 6 July 2015.
  6. Moonhee Jang; Ilchung Shin; Jihyun Kim; Wonkyung Yang (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.
  7. Ritva Karinen; Silja Skogstad Tuv; Elisabeth Leere Øiestad; Vigdis Vindenes (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.
  8. Niels Bjerre Holm; Anders Just Pedersen; Petur Weihe Dalsgaard; Kristian Linnet (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.
  9. Ariane Wohlfarth; Marisol S. Castaneto; Mingshe Zhu; Shaokun Pang; Karl B. Scheidweiler; Robert Kronstrand; Marilyn A. Huestis (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.
  10. Hess, Cornelius; Schoeder, ClaraT.; Pillaiyar, Thanigaimalai; Madea, Burkhard; Müller, ChristaE. (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. ISSN 1860-8965. PMC 4929166. PMID 27429655.
  11. "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.
  12. "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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  13. "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.
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