AM-2233

AM-2233

Legal status
Legal status	CA: Schedule II DE: Anlage II (Prohibited) Temporary Class Drug (NZ)
Identifiers
IUPAC name 1-[(N-methylpiperidin-2-yl)methyl]-3-(2-iodobenzoyl)indole
CAS Number	444912-75-8
PubChem (CID)	10226340
ChemSpider	8401830
ChEMBL	CHEMBL364266
Chemical and physical data
Formula	C22H23IN2O
Molar mass	458.334 g/mol
3D model (Jmol)	Interactive image
SMILES Ic3ccccc3C(=O)c1cn(CC2CCCCN2C)c4c1cccc4
InChI InChI=1S/C22H23IN2O/c1-24-13-7-6-8-16(24)14-25-15-19(17-9-3-5-12-21(17)25)22(26)18-10-2-4-11-20(18)23/h2-5,9-12,15-16H,6-8,13-14H2,1H3 Key:KSLCYQTUSSEGPT-UHFFFAOYSA-N
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AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a K_i 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

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

See also

• AM-679
• AM-694
• AM-1220
• AM-1221
• AM-1235
• AM-1241
• AM-2232
• Cannabipiperidiethanone
• FUBIMINA
• JWH-018
• List of AM cannabinoids
• List of JWH cannabinoids

References

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.
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.
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.
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. PMC 3212432. PMID 21836461.
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.