5F-APINACA

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5F-APINACA
5F-APINACA.png
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C23H30FN3O
Molar mass 383.5 g/mol
3D model (JSmol)

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]

Pharmacology[edit]

5F-AKB-48 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[edit]

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]

See also[edit]

References[edit]

  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. PMC 4406957Freely accessible. 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 4929166Freely accessible. 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. 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.