5F-APINACA (also known as A-5F-PINACA,[3] 5F-AKB-48 or 5F-AKB48) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.[4][5] 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.[6]
Quick Facts Clinical data, Other names ...
5F-APINACA |
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| Other names | 5F-AKB-48, 5F-AKB48 |
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N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide
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| Formula | C23H30FN3O |
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| Molar mass | 383.511 g·mol−1 |
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O=C(NC1(C[C@@H]2C3)C[C@H](C2)C[C@H]3C1)C4=NN(CCCCCF)C5=CC=CC=C54
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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
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5F-APINACA was first identified in South Korea.[7] It is expected to be a potent agonist of the CB1 receptor and CB2 receptor.[8] Its metabolism has been described in literature.[9][10][11][12]
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.[13]
In the United States, 5F-APINACA is a Schedule I controlled substance.[14]
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.[15]
5F-APINACA is banned in the Czech Republic.[16]
Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325. "5F-AKB48" (PDF). Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG). 18 February 2013. Retrieved 6 July 2015. Chung H, Choi H, Heo S, Kim E, Lee J (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. S2CID 23058813. Jang M, Shin I, Kim J, Yang W (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. S2CID 3038555. Karinen R, Tuv SS, Øiestad EL, Vindenes V (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. Holm NB, Pedersen AJ, Dalsgaard PW, Linnet K (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. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
