5F-APINACA

Not to be confused with 5F-AB-PINACA.
5F-APINACA
Systematic (IUPAC) name
N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide
Legal status
Legal status
Identifiers
CAS Number 1400742-13-3
PubChem CID 71711119
ChemSpider 29339965
Chemical data
Formula C23H30FN3O
Molar mass 383.5 g/mol

5F-APINACA (also known as 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]

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]

Legality

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.[10]

5F-APINACA is banned in the Czech Republic.[11]

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: 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. PMID 25721194.
  10. ↑ "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. Retrieved 1 October 2015.
  11. ↑ "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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