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 names	5F-AKB-48, 5F-AKB48
Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) US: Schedule I
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
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.[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]

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. "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.

External links

• Abouchedid, Rachelle; Ho, James H.; Hudson, Simon; Dines, Alison; Archer, John R. H.; Wood, David M.; Dargan, Paul I. (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.