APINACA

APINACA (AKB48, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide) is a drug that acts as a reasonably potent agonist for the cannabinoid receptors.[2] It is a full agonist at CB1 with an EC50 of 142 nM[3] and Ki of 3.24 nM (compared to the Ki of Δ9-THC at 28.35 nM and JWH-018 at 9.62 nM),[4] while at CB2 it acts as a partial agonist with an EC50 of 141 nM[3] and Ki of 1.68 nM (compared to the Ki of Δ9-THC at 37.82 nM and JWH-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 in synthetic cannabis smoking blends, along with a related compound APICA.[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.

This article is about the synthetic cannabinoid drug. For the Japanese girl idol group, see AKB48.

APINACA
Legal status
Legal status
Identifiers
  • N-(1-Adamantyl)-1-pentylindazole-3-carboxamide
CAS Number
  • 1345973-53-6 checkY (1-adamantyl isomer)
    1400742-54-2 (2-adamantyl isomer)
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H31N3O
Molar mass365.521 g·mol−1
3D model (JSmol)
  • C3C4CC2CC3CC(C4)(C2)NC(=O)c(nn1CCCCC)c5c1cccc5
  • InChI=1S/C23H31N3O/c1-2-3-6-9-26-20-8-5-4-7-19(20)21(25-26)22(27)24-23-13-16-10-17(14-23)12-18(11-16)15-23/h4-5,7-8,16-18H,2-3,6,9-15H2,1H3,(H,24,27)
  • Key:UCTCCIPCJZKWEZ-UHFFFAOYSA-N

Legality

APINACA was made illegal in Japan in 2012,[8] and was banned as a temporary class drug in New Zealand from 13 July 2012.[9]

APINACA has been banned in Latvia since 14 November 2013.

Since 2013, APINACA has been a Schedule I controlled substance in the United States.[10]

It is also banned in Germany as an Anlage II controlled drug.

APINACA is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.[11]

As of October 2015 APINACA is a controlled substance in China.[12]

APINACA is banned in the Czech Republic.[13]

Detection

A forensic standard of APINACA is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[14]

See also

References
  1. Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  2. 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. PMID 23063179.
  3. Longworth M, Reekie TA, Blakey K, Boyd R, Connor M, Kassiou M (July 2019). "New-generation azaindole-adamantyl-derived synthetic cannabinoids". Forensic Toxicology. 37 (2): 350–365. doi:10.1007/s11419-019-00466-1.
  4. Canazza 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. PMID 27527584.
  5. CN application 111518095A, "Azaindole derivatives, and preparation method and application thereof", published 2020-08-11. See compound no. 37.
  6. 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. S2CID 44193953.
  7. WO 2003035005A2, "Heteroindanes: a new class of potent cannabimimetic ligands", published 2003-05-01
  8. "Designation of "Shitei Yakubutsu" (designated substances) based on the provision of the Pharmaceutical Affairs Law (1960, Law No.145)" (PDF).
  9. "Temporary Class Drug Notice". Department of Internal Affairs. New Zealand. 5 July 2012.
  10. "DEA Makes Three More "Fake Pot" Drugs Temporarily Illegal Today". Drug Enforcement Administration (DEA). Retrieved 24 July 2015.
  11. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  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. Archived from the original (PDF) on 9 March 2016. Retrieved 6 February 2016.
  14. "APINACA". Southern Association of Forensic Scientists. Archived from the original on 24 July 2015. Retrieved 24 July 2015.
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