AM-694
Legal status
Legal status
Identifiers
  • 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H19FINO
Molar mass435.281 g·mol−1
3D model (JSmol)
  • Ic2ccccc2C(=O)c1cn(CCCCCF)c3ccccc13
  • InChI=1S/C20H19FINO/c21-12-6-1-7-13-23-14-17(15-8-3-5-11-19(15)23)20(24)16-9-2-4-10-18(16)22/h2-5,8-11,14H,1,6-7,12-13H2 checkY
  • Key:LFFIIZFINPPEMC-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[1]

Pharmacology

AM-694 is an agonist for cannabinoid receptors. It has a Ki of 0.08 nM at CB1 and 18 times selectivity over CB2 with a Ki of 1.44 nM.[2] 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.[1]

Metabolism

Pathways of metabolism include hydrolytic defluorination, carboxylation, and monohydroxylation of the N-alkyl chain.[3][4]

See also

References

  1. 1 2 Willis PG, Katoch-Rouse R, Horti AG (August 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.
  2. ↑ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
  3. ↑ Grigoryev A, Kavanagh P, Melnik A (February 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): 110–5. doi:10.1002/dta.1336. PMID 22522907.
  4. ↑ Apirakkan O, Gavrilović I, Cowan DA, Abbate V (July 2020). "In Vitro Phase I Metabolic Profiling of the Synthetic Cannabinoids AM-694, 5F-NNEI, FUB-APINACA, MFUBINAC, and AMB-FUBINACA". Chemical Research in Toxicology. 33 (7): 1653–1664. doi:10.1021/acs.chemrestox.9b00466. PMID 32301604. S2CID 215803607.
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