AM-1221
AM-1221 structure.png
Legal status
Legal status
Identifiers
  • 1-[(N-Methylpiperidin-2-yl)methyl]-2-methyl-3-(naphthalen-1-oyl)-6-nitroindole
CAS Number
  • 335160-53-7 ☒N
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H27N3O3
Molar mass441.531 g·mol−1
3D model (JSmol)
  • CN1CCCCC1CN2C=C(C3=C2C=C(C=C3)[N+](=O)[O-])C(=O)C4=CC=CC5=CC=CC=C54
  • 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 checkY
  • Key:QGNIEJBBHMMNOZ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

AM-1221 is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB2, with a Ki of 0.28 nM at CB2 and 52.3 nM at the CB1 receptor, giving it around 180 times 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]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as AM-1221 are Schedule I Controlled Substances.[4]

Legal Status[edit]

It's illegal supply, trade, sell, distribute, import or transport the pharmaceutical drug under the Psychoactive Substances Act 2016 which was inforce on May26th 2016.

SEE ALSO[edit]

References[edit]

  1. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  2. ^ Deng H (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (Ph.D. Dissertation). University of Connecticut. ProQuest 304624325.
  3. ^ Manera C, Tuccinardi T, Martinelli A (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.
  4. ^ 21 U.S.C. § 812: Schedules of controlled substances