AM-694

AM-694

File:AM-694-2D-skeletal.svg
Systematic (IUPAC) name
1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone
Legal status
Legal status	Legal
Identifiers
PubChem	CID 9889172
Chemical data
Formula	C20H19FINO
Molar mass	435.273 g/mol[[]]

AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a drug which acts as a potent and selective agonist for the cannabinoid receptor CB₁, with a Ki of 0.08nM at CB₁ and 18x selectivity over the related CB₂ receptor. 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.. No public data about AM-694 metabolism is known.

AM-694 has already emerged as a designer drug. Concerns have been raised over the possible toxicity of this compound, due to its likely metabolism to ω-fluoroalkanoic acids. Studies of the metabolism of related compounds show that the first step is the N-dealkylation of the indole nitrogen, which in this case yields 5-fluoropentanoic acid, which is then further metabolised to 3-fluoropropanoic acid. Terminal monofluoroalkanes with even numbers of carbons are ultimately metabolized into fluoroacetate, which is a potent toxin primarily used as a rodenticide and has the potential to bioaccumulate. As AM-694 contains a five carbon chain, fluoroacetate is unlikely to be produced as a metabolite, with the substantially less toxic 3-fluoropropanoic acid being produced instead. The 4-fluorobutyl and 6-fluorohexyl homologues of AM-694 will however produce fluoroacetate as a metabolite and so may be significantly more toxic. Fluoroacetate is also produced in similar fashion by S-dealkylation of 2C-T-21, another designer drug, so death from acute fluoroacetate poisoning appears unlikely following consumption of these drugs, with concerns instead relating to the potential for chronic toxicity with extended use.