AM-2233

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AM-2233
AM-2233 structure.png
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
ECHA InfoCard 100.233.382
Chemical and physical data
Formula C22H23IN2O
Molar mass 458.334 g/mol
3D model (JSmol)
 NYesY (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 1.8 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]

Legal Status[edit]

As of October 2015 AM-2233 is a controlled substance in China.[9]

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. PMID 16190764. doi:10.1021/jm050135l. 
  3. ^ Hanuš, L. R. O.; Mechoulam, R. (2005). "Cannabinoid chemistry: an overview". Cannabinoids as Therapeutics. Milestones in Drug Therapy MDT. p. 23. ISBN 3-7643-7055-6. doi:10.1007/3-7643-7358-X_2. 
  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. PMID 16438957. doi:10.1016/j.ejphar.2005.12.026. 
  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. PMID 16715483. doi:10.1002/syn.20277. 
  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. PMC 3700404Freely accessible. PMID 19022181. doi:10.1016/j.chembiol.2008.10.011. 
  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. PMC 3212432Freely accessible. PMID 21836461. doi:10.1097/FBP.0b013e328349fbd5. 
  9. ^ "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. Retrieved 1 October 2015.