AM-694

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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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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

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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

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

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Finland

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AM-694 is scheduled in the "government decree on psychoactive substances banned from the consumer market".[5]

See also

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References

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  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
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