AM-2233

AM-2233

Systematic (IUPAC) name
1-[(N-methylpiperidin-2-yl)methyl]-3-(2-iodobenzoyl)indole
Clinical data
Pregnancy cat.	?
Legal status	Temporary Class Drug (NZ)
Identifiers
CAS number	444912-75-8 N
ATC code	?
PubChem	CID 10226340
ChemSpider	8401830 Y
ChEMBL	CHEMBL364266 Y
Chemical data
Formula	C22H23IN2O
Mol. mass	458.334 g/mol
SMILES	eMolecules & PubChem
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 Y Key:KSLCYQTUSSEGPT-UHFFFAOYSA-N Y
N (what is this?)  (verify)

AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a K_i 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

• AM-679
• AM-694
• AM-1220
• AM-1221
• AM-1241
• Cannabipiperidiethanone

References

1. ^ Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
2. ^ Deng H, Gifford AN, Zvonok AM, Cui G, Li X, Fan P, Deschamps JR, Flippen-Anderson JL, Gatley SJ, Makriyannis A (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. ^ Hanu�, L. �R. O.; Mechoulam, R. (2005). Cannabinoid chemistry: an overview. pp. 23. doi:10.1007/3-7643-7358-X_2.  edit
4. ^ 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): 41–6. 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. doi:10.1002/syn.20277. PMID 16715483.  edit
6. ^ Leung K (2006 Dec 12). "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.; Mercier, R.; Anday, J.; Thakur, G.; Zvonok, A.; Hurst, D.; Reggio, P.; Janero, D. 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. 

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