AM-694

AM-694
AM-694-2D-skeletal.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H19FINO
Molar mass435.281 g·mol−1
3D model (JSmol)
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AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a designer drug that acts as a potent and selective agonist for the cannabinoid receptor CB1. It is used in scientific research for mapping the distribution of CB1 receptors.[citation needed]

Pharmacology[edit]

AM-694 is an agonist for cannabinoid receptors. Affinities are: with a Ki of 0.08 nM at CB1 and 18x selectivity over CB2 with a Ki of 1.44 nM.[1] It is unclear what is responsible for this unusually high CB1 binding affinity, but it makes the 18F radiolabelled derivative of AM-694 useful for mapping the distribution of CB1 receptors in the body.[2]

Metabolism[edit]

Pathways of metabolism include hydrolytic defluorination, carboxylation, and monohydroxylation of the N-alkyl chain.[3]

See also[edit]

References[edit]

  1. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  2. ^ Willis, Peter G.; Katoch-Rouse, Reeti; Horti, Andrew G. (2003). "Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand". Journal of Labelled Compounds and Radiopharmaceuticals. 46 (9): 799–804. doi:10.1002/jlcr.720.
  3. ^ Grigoryev, Andrej; Kavanagh, Pierce; Melnik, Aleksandra (2013). "The detection of the urinary metabolites of 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (AM-694), a high affinity cannabimimetic, by gas chromatography - mass spectrometry". Drug Testing and Analysis. 5 (2): 110–115. doi:10.1002/dta.1336. PMID 22522907.