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| Formula | C24H32N2O |
| Molar mass | 364.533 g·mol−1 |
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APICA (2NE1,SDB-001,N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide) is anindole based drug that acts as a potentagonist for thecannabinoid receptors.[1]
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 its indazole derivativeAPINACA (sold as "AKB48").[2]
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. Given the known metabolic liberation (and presence as an impurity) ofamantadine in the related compoundAPINACA, it is suspected that metabolichydrolysis of the amide group of APICA may also release amantadine.
Pharmacological testing determined APICA to have anIC50 of 175 nM at CB1, only slightly less potent than JWH-018 which had an IC50 of 169 nM, but over four times more tightly binding than APINACA, which had an IC50 of 824 nM.[3] 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).[4] Furthermore, APICA possesses cannabis-like effects in rats, and appears to be less potent thanJWH-018 but more potent than THC.[4][5]
As of October 2015, APICA is a controlled substance in China.[6]
