<unk> (2NE1, SDB-001, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide) is an indole based 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 its indazole derivative<unk> CA (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. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound<unk> CA, it is suspected that metabolic hydrolysis of the amide group of<unk> may also release amantadine. Pharmacological testing determined<unk> to have an IC50 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<unk> CA, which had an IC50 of 824 nM. The first published synthesis and pharmacological evaluation of<unk> revealed that it acts as a full agonist at CB1 (EC50 = 34 nM) and CB2 receptors (EC50 = 29 nM). Furthermore,<unk> possesses cannabis-like effects in rats, and appears to be less potent than JWH-018 but more potent than THC.
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