APICA (synthetic cannabinoid drug)
|Systematic (IUPAC) name|
|CAS Registry Number|
|Molecular mass||364.522 g/mol|
APICA (2NE1, SDB-001, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide) is a drug that acts as a potent agonist for the cannabinoid receptors. 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 APINACA (sold as "AKB48"). Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with an indole core instead of indazole, and a simple pentyl chain on the indole 1-position. Pharmacological testing determined APICA to have an IC50 of 175nM at CB1, only slightly less potent than JWH-018 which had an IC50 of 169nM, but over four times more tightly binding than AKB48, which had an IC50 of 824nM. The first published synthesis and pharmacological evaluation of APICA revealed that it acts as a full agonist at CB1 (EC50 = 34 nM) and CB2 receptors (EC50 = 29 nM). Furthermore, APICA possesses cannabis-like effects in rats, and appears to be less potent than JWH-018 but more potent than THC.
- STS-135 (drug)
- 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. doi:10.1007/s11419-012-0136-7.
- 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. doi:10.1016/j.forsciint.2012.08.047. PMID 23063179.
- Banister, S. D.; Wilkinson, S. M.; Longworth, M.; Stuart, J.; Apetz, N.; English, K.; Brooker, L.; Goebel, C.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: Novel cannabimimetic drugs of abuse". ACS Chemical Neuroscience 4 (7): 130403084729007. doi:10.1021/cn400035r.
- Banister, S. D.; Stuart, J.; Kevin, R. C.; Edington, A.; Longworth, M.; Wilkinson, S. M.; Beinat, C.; Buchanan, A. S.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (2015). "Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135". ACS Chemical Neuroscience: 150508124201002. doi:10.1021/acschemneuro.5b00107.
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