Cannabaceae

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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[edit]

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[edit]

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

See also[edit]

References[edit]

  1. ^ a b 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.
source: https://en.wikipedia.org/wiki/AM-694

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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