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AM-1248

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AM-1248
Identifiers
IUPAC name
  • 1--3-(adamant-1-oyl)indole
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H34N2O
Molar mass390.561 g/mol g·mol
3D model (JSmol)
SMILES
  • CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5
  (verify)

AM-1248 is a drug which acts as a moderately potent agonist for both the cannabinoid receptors CB1 and CB2, but with some dispute between sources over its exact potency and selectivity. Replacing the 3-(1-naphthoyl) group found in many indole derived cannabinoid ligands, with an adamantoyl group, generally confers significant CB2 selectivity, but reasonable CB1 affinity and selectivity is retained when an N-methylpiperidin-2-ylmethyl substitution is used at the indole 1-position. The related compound 1-pentyl-3-(1-adamantoyl)indole was identified as having been sold as a cannabinoid designer drug in Hungary in 2011, along with another synthetic cannabinoid AM-679.

See also

References

  1. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm901214q, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm901214q instead.
  2. US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26 
  3. WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  4. Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J (2011). "Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary". Forensic Science International. doi:10.1016/j.forsciint.2011.07.011. PMID 21813254. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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