APINACA (AKB48,N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide) is a drug that acts as a reasonably potentagonist for thecannabinoid receptors.[2] It is a full agonist atCB1 with an EC50 of 142 nM[3] and Ki of 3.24 nM (compared to the Ki ofΔ9-THC at 28.35 nM andJWH-018 at 9.62 nM),[4] while atCB2 it acts as a partial agonist with an EC50 of 141 nM[3] and Ki of 1.68 nM (compared to the Ki ofΔ9-THC at 37.82 nM andJWH-018 at 8.55 nM).[4] Its pharmacological characterization has also been reported in a discontinued patent application.[5] It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in March 2012 as an ingredient insynthetic cannabis smoking blends, along with a related compoundAPICA.[6] Structurally, it closely resembles cannabinoid compounds from a University of Connecticut patent,[7] but with a simple pentyl chain on the indazole 1-position, and APINACA falls within the claims of this patent despite not being disclosed as an example.
^Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (April 2013). "URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products".Forensic Science International.227 (1–3):21–32.doi:10.1016/j.forsciint.2012.08.047.PMID23063179.
^abCanazza I, Ossato A, Trapella C, Fantinati A, De Luca MA, Margiani G, et al. (October 2016). "Effect of the novel synthetic cannabinoids AKB48 and 5F-AKB48 on "tetrad", sensorimotor, neurological and neurochemical responses in mice. In vitro and in vivo pharmacological studies".Psychopharmacology.233 (21–22):3685–3709.doi:10.1007/s00213-016-4402-y.hdl:11392/2352324.PMID27527584.
^CN application 111518095A, "Azaindole derivatives, and preparation method and application thereof", published 11 August 2020. See compound no. 37.
^Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012). "Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products".Forensic Toxicology.30 (2):114–125.doi:10.1007/s11419-012-0136-7.S2CID44193953.
^WO 2003035005A2, "Heteroindanes: a new class of potent cannabimimetic ligands", published 1 May 2003
^"CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived fromthe original on 15 July 2015. Retrieved24 July 2015.
^"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 fromthe original on 1 October 2015. Retrieved1 October 2015.
