AM-679 (cannabinoid)

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This article is about the cannabinoid agonist. For the FLAP inhibitor, see AM-679 (FLAP inhibitor).
AM-679 (cannabinoid)
AM-679 structure.png
Legal status
Legal status
  • CA: Schedule II
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
IUPAC name
  • (2-Iodophenyl)(1-pentyl-1H-indol-3-yl)methanone
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H20INO
Molar mass417.290 g·mol−1
3D model (JSmol)
SMILES
  • Ic1ccccc1C(=O)c(c2ccccc23)cn3CCCCC
InChI
  • InChI=1S/C20H20INO/c1-2-3-8-13-22-14-17(15-9-5-7-12-19(15)22)20(23)16-10-4-6-11-18(16)21/h4-7,9-12,14H,2-3,8,13H2,1H3 checkY
  • Key:GAJBHYUAJOTAEW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  

AM-679 (part of the AM cannabinoid series) is a drug that acts as a moderately potent agonist for the cannabinoid receptors, with a Ki of 13.5 nM at CB1 and 49.5 nM at CB2.[1] AM-679 was one of the first 3-(2-iodobenzoyl)indole derivatives that was found to have significant cannabinoid receptor affinity, and while AM-679 itself has only modest affinity for these receptors, it was subsequently used as a base to develop several more specialised cannabinoid ligands that are now widely used in research, including the potent CB1 agonists AM-694 and AM-2233, and the selective CB2 agonist AM-1241.[2] AM-679 was first identified as having been sold as a cannabinoid designer drug in Hungary in 2011, along with another novel compound 1-pentyl-3-(1-adamantoyl)indole.[3]

See also[]

References[]

  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 (PhD Dissertation). University of Connecticut. ProQuest 304624325.
  3. ^ Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J (January 2012). "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. doi:10.1016/j.forsciint.2011.07.011. PMID 21813254.
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