AM-1221

AM-1221

Legal status
Legal status	CA: Schedule II
Identifiers
IUPAC name 1-[(N-methylpiperidin-2-yl)methyl]-2-methyl-3-(naphthalen-1-oyl)-6-nitroindole
CAS Number	335160-53-7
PubChem (CID)	11604318
ChemSpider	26286945
UNII	SHC6SNM293
Chemical and physical data
Formula	C27H27N3O3
Molar mass	441.521 g/mol
3D model (Jmol)	Interactive image
SMILES c5ccc2ccccc2c5C(=O)c(c4ccc([N](=O)=O)cc14)c(C)n1CC3CCCCN3C
InChI InChI=1S/C27H27N3O3/c1-18-26(27(31)23-12-7-9-19-8-3-4-11-22(19)23)24-14-13-20(30(32)33)16-25(24)29(18)17-21-10-5-6-15-28(21)2/h3-4,7-9,11-14,16,21H,5-6,10,15,17H2,1-2H3 Key:QGNIEJBBHMMNOZ-UHFFFAOYSA-N
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AM-1221 is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB₂, with a K_i of 0.28 nM at CB₂ and 52.3 nM at the CB₁ receptor, giving it around 180x selectivity for CB₂.^[1] The 2-methyl and 6-nitro groups on the indole ring both tend to increase CB₂ affinity while generally reducing affinity at CB₁, explaining the high CB₂ selectivity of AM-1221. However, despite this relatively high selectivity for CB₂, its CB₁ affinity is still too strong to make it useful as a truly selective CB₂ agonist, so the related compound AM-1241 is generally preferred for research purposes.^[2][3]

See also

• AM-630
• AM-1220
• AM-1235
• AM-2233
• UR-144
• N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide

References

1. WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
2. Hongfeng Deng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut.
3. Manera, C; Tuccinardi, T; Martinelli, A (2008). "Indoles and related compounds as cannabinoid ligands". Mini reviews in medicinal chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.