APICA (synthetic cannabinoid drug)

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APICA (synthetic cannabinoid drug)
Legal status
Legal status
Identifiers
  • N-(1-Adamantyl)-1-pentylindole-3-carboxamide
JSmol)
  • CCCCCn1cc(C(=O)NC23CC4CC(CC(C4)C2)C3)c5ccccc15
  • InChI=1S/C24H32N2O/c1-2-3-6-9-26-16-21(20-7-4-5-8-22(20)26)23(27)25-24-13-17-10-18(14-24)12-19(11-17)15-24/h4-5,7-8,16-19H,2-3,6,9-15H2,1H3,(H,25,27)
  • Key:MDJYHWLDDJBTMX-UHFFFAOYSA-N

APICA (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.[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 in

synthetic cannabis smoking blends, along with its indazole derivative APINACA (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) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of APICA may also release amantadine.

Pharmacological testing determined APICA 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 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 than JWH-018 but more potent than THC.[4][5]

Legal Status

As of October 2015 APICA is a controlled substance in China.[6]

See also

References

  1. PMID 26826846
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  6. ^ "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.