AM-694

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Chemical compound

title: "AM-694" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["benzoylindoles", "2-iodophenyl-compounds", "organofluorides", "am-cannabinoids", "designer-drugs", "pet-radiotracers"] description: "Chemical compound" topic_path: "general/benzoylindoles" source: "https://en.wikipedia.org/wiki/AM-694" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | verifiedrevid = 477235914 | IUPAC_name = 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone | image = AM-694-2D-skeletal.svg | image_class = skin-invert-image

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = S9 | legal_CA = Schedule II | legal_UK = Class B | legal_US = Schedule I | legal_DE = Anlage II | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 335161-03-0 | UNII_Ref = | UNII = 6RK7KN7L1O | ATC_prefix = | ATC_suffix = | PubChem = 9889172 | ChEBI = 138017 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 8064843

| C=20 | H=19 | F=1 | I=1 | N=1 | O=1 | smiles = Ic2ccccc2C(=O)c1cn(CCCCCF)c3ccccc13 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = LFFIIZFINPPEMC-UHFFFAOYSA-N

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.

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. 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.

Metabolism

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

Legal status

Finland

AM-694 is scheduled in the "government decree on psychoactive substances banned from the consumer market".

References

References

  1. (August 2003). "Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand". Journal of Labelled Compounds and Radiopharmaceuticals.
  2. "Cannabimimetic indole derivatives".
  3. (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.
  4. (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.
  5. "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | 1130/2014 | Lainsäädäntö | Finlex".

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

benzoylindoles2-iodophenyl-compoundsorganofluoridesam-cannabinoidsdesigner-drugspet-radiotracers