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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 whom?date=May 2011 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.
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