AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a Ki of 1.8 nM at CB1 and 2.2 nM at CB2 as the active (R) enantiomer.[1] It was developed as a selective radioligand for the cannabinoid receptors and has been used as its 131I derivative for mapping the distribution of the CB1 receptor in the brain.[2][3][4][5][6][7] AM-2233 was found to fully substitute for THC in rats, with a potency lower than that of JWH-018 but higher than WIN 55,212-2.[8]
It is notable for inducing tinnitus,[9] though the reasons for this are unclear and may provide valuable insight into tinnitus research.
Legal Status
As of October 2015 AM-2233 is a controlled substance in China.[10]
^Hongfeng Deng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD Dissertation). University of Connecticut. ProQuest304624325.
^Deng H, Gifford AN, Zvonok AM, Cui G, Li X, Fan P, et al. (October 2005). "Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor". Journal of Medicinal Chemistry. 48 (20): 6386–6392. doi:10.1021/jm050135l. PMID16190764.
^Hanuš LR, Mechoulam R (2005). "Cannabinoid chemistry: an overview". Cannabinoids as Therapeutics. Milestones in Drug Therapy MDT. pp. 23–46. doi:10.1007/3-7643-7358-X_2. ISBN978-3-7643-7055-8.
^Shen CP, Xiao JC, Armstrong H, Hagmann W, Fong TM (February 2006). "F200A substitution in the third transmembrane helix of human cannabinoid CB1 receptor converts AM2233 from receptor agonist to inverse agonist". European Journal of Pharmacology. 531 (1–3): 41–46. doi:10.1016/j.ejphar.2005.12.026. PMID16438957.
^Dhawan J, Deng H, Gatley SJ, Makriyannis A, Akinfeleye T, Bruneus M, et al. (August 2006). "Evaluation of the in vivo receptor occupancy for the behavioral effects of cannabinoids using a radiolabeled cannabinoid receptor agonist, R-[125/131I]AM2233". Synapse. 60 (2): 93–101. doi:10.1002/syn.20277. PMID16715483. S2CID21269336.
^Leung K (Dec 12, 2006). "R-2-[131I]Iodophenyl-(1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl)methanone". Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. PMID20641836.
^"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.
