AM-1235

AM-1235

AM-1235

Systematic (IUPAC) name
1-[(5-fluoropentyl)-6-nitro-1H-indol-3-yl]-(naphthalen-1-yl)methanone
Identifiers
ATC code	?
Chemical data
Formula	C24H21FN2O3
Mol. mass	404.433 g/mol
SMILES	eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.	?
Legal status	?

AM-1235 (1-(5-fluoropentyl)-3-(naphthalen-1-oyl)-6-nitroindole) is a drug which acts as a potent and reasonably selective agonist for the cannabinoid receptor CB₁, with a K_i of 1.5nM at CB₁ compared to 20.4nM at CB₂. While the 6-nitro substitution on the indole ring reduces affinity for both CB₁ and CB₂ relative to the unsubstituted parent compound AM-2201, CB₂ affinity is reduced much more, resulting in a CB₁ selectivity of around 13x. This is in contrast to other related compounds such as AM-1221 where a 6-nitro substitution instead confers significant selectivity for CB₂.

References

1. US patent 7241799, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2007-07-10
2. Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
3. WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07

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