Apinaca

APINACA

Systematic (IUPAC) name
1-pentyl-N-tricyclo[3.3.1.13,7]dec-1-yl-1H-indazole-3-carboxamide
Clinical data
Legal status	Illegal (US), Temporary Class Drug (NZ), illegal in Japan, illegal in Latvia Schedule I in USA
Identifiers
CAS number	Y
ATC code	?
ChemSpider
Chemical data
Formula	C23H31N3O
Mol. mass	365.510 g/mol
SMILES C3C4CC2CC3CC(C4)(C2)NC(=O)c(nn1CCCCC)c5c1cccc5
InChI 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

AKB48 (APINACA, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide) is a drug that acts as a reasonably potent agonist for the cannabinoid receptors,^[1] with a K_i of 304.5nM and a EC₅₀ of 585nM at CB₁. 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.^[2] Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a simple pentyl chain on the indazole 1-position, and AKB48 falls within the claims of this patent despite not being disclosed as an example. AKB48 was made illegal in Japan in 2012,^[3] and was banned as a temporary class drug in New Zealand from 13 July 2012.^[4] It has been banned in Latvia since 14 November 2013. The DEA announced its intent to schedule 16 May 2013. ^[5]

Detection

A forensic standard of AKB48 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.^[6]

See also

• AB-001
• AB-FUBINACA
• AB-PINACA
• ADB-FUBINACA
• ADB-PINACA
• RCS-4
• RCS-8
• SDB-001
• STS-135

References

1. ^ Uchiyama, N.; Kawamura, M.; Kikura-Hanajiri, R.; Goda, Y. (2012). "URB-754: A new class of designer drug and 12 synthetic cannabinoids detected in illegal products". Forensic Science International 227 (1–3): 21–32.  
2. ^ 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.  
3. ^ "Designation of "Shitei Yakubutsu" (designated substances) based on the provision of the Pharmaceutical Affairs Law (1960, Law No.145)" (PDF). 
4. ^ "Temporary Class Drug Notice". Department of Internal Affairs. New Zealand. 5 July 2012. 
5. ^ url=http://www.justice.gov/dea/divisions/hq/2013/hq051613.shtml
6. ^ http://forendex.southernforensic.org/detail/index/1221

• http://www.gpo.gov/fdsys/pkg/FR-2013-04-12/html/2013-08671.htm