AM-1248

AM-1248

AM-1248
Systematic (IUPAC) name
1-[(N-methylpiperidin-2-yl)methyl]-3-(adamant-1-oyl)indole
Clinical data
Legal status
  • Temporary Class Drug (NZ)
Identifiers
CAS number  N
ATC code ?
PubChem
Chemical data
Formula C26H34N2O 
Mol. mass 390.561 g/mol
 N   

AM-1248 is a drug that 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,[1] but reasonable CB1 affinity and selectivity is retained when an N-methylpiperidin-2-ylmethyl substitution is used at the indole 1-position.[2][3] 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.[4]

See also

References

  1. ^ Frost, J. M., et al. (2010). "Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity". Journal of Medicinal Chemistry 53 (1): 295–315.  
  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, et al. (August 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 214 (1-3): 27–32.