AM-2233

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AM-2233
AM-2233 structure.png
Systematic (IUPAC) name
1-[(N-methylpiperidin-2-yl)methyl]-3-(2-iodobenzoyl)indole
Clinical data
Legal status Temporary Class Drug (NZ)
Identifiers
CAS number 444912-75-8 N
ATC code ?
PubChem CID 10226340
ChemSpider 8401830 YesY
ChEMBL CHEMBL364266 YesY
Chemical data
Formula C22H23IN2O 
Mol. mass 458.334 g/mol
 N (what is this?)  (verify)

AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a Ki of 1.8nM at CB1 and 2.2nM 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]

See also[edit]

References[edit]

  1. ^ Hongfeng Deng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD Dissertation). University of Connecticut. 
  2. ^ Deng H, et al. (October 2005). "Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor". Journal of Medicinal Chemistry 48 (20): 6386–92. doi:10.1021/jm050135l. PMID 16190764. 
  3. ^ Hanuš, L. R. O.; Mechoulam, R. (2005). "Cannabinoid chemistry: an overview". Cannabinoids as Therapeutics. Milestones in Drug Therapy MDT. p. 23. doi:10.1007/3-7643-7358-X_2. ISBN 3-7643-7055-6.  edit
  4. ^ Shen CP, et al. (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): 41–6. doi:10.1016/j.ejphar.2005.12.026. PMID 16438957. 
  5. ^ Dhawan, J.; Deng, H.; Gatley, S. J.; Makriyannis, A.; Akinfeleye, T.; Bruneus, M.; Dimaio, A. A.; Gifford, A. N. (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. PMID 16715483.  edit
  6. ^ 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]. PMID 20641836. 
  7. ^ Pei, Y., et al. (2008). "Ligand-Binding Architecture of Human CB2 Cannabinoid Receptor: Evidence for Receptor Subtype-Specific Binding Motif and Modeling GPCR Activation". Chemistry & Biology 15: 1207. doi:10.1016/j.chembiol.2008.10.011.  edit
  8. ^ Järbe TU, Deng H, Vadivel SK, Makriyannis A (September 2011). "Cannabinergic aminoalkylindoles, including AM678=JWH018 found in 'Spice', examined using drug (Δ9-tetrahydrocannabinol) discrimination for rats". Behavioural Pharmacology 22 (5-6): 498–507. doi:10.1097/FBP.0b013e328349fbd5. PMID 21836461.