AM-1235

AM-1235

Systematic (IUPAC) name
1-[(5-fluoropentyl)-6-nitro-1H-indol-3-yl]-(naphthalen-1-yl)methanone
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	335161-27-8 Y
ATC code	?
ChemSpider	26633899
Chemical data
Formula	C24H21FN2O3
Mol. mass	404.433 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C24H21FN2O3/c25-13-4-1-5-14-26-16-22(20-12-11-18(27(29)30)15-23(20)26)24(28)21-10-6-8-17-7-2-3-9-19(17)21/h2-3,6-12,15-16H,1,4-5,13-14H2 Key:LNGVQORPSNNMSZ-UHFFFAOYSA-N
Y (what is this?)  (verify)

AM-1235 (1-(5-fluoropentyl)-3-(naphthalen-1-oyl)-6-nitroindole) is a drug that 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.^[1] 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.^[2] This is in contrast to other related compounds such as AM-1221 where a 6-nitro substitution instead confers significant selectivity for CB₂.^[3]

See also

• AM-906
• AM-2389
• O-1812

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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