2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine is a drug originally researched as a potential opioid analgesic, but was found to be inactive in this assay, and relatively toxic to mice.[1] Subsequently it was found to possess activity as an agonist at nicotinic acetylcholine receptors during the course of work that ultimately led to the discovery of the anti-smoking drug varenicline.[2][3]
More recently this chemical compound is claimed to have been sold as a designer drug under the name A3A,[citation needed] but since the anecdotally reported effects of the product sold under this name do not seem to bear any resemblance to the known pharmacology of genuine 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine, it seems unlikely that this is actually the compound being sold.
↑"Synthesis and pharmacological activity of 2,3,4,5,-tetrahydro-1,5-methano-1H-3-benzazepines". Journal of Medicinal Chemistry22 (4): 455–457. April 1979. doi:10.1021/jm00190a020. PMID430484.
↑"Synthesis of 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine via Oxidative Cleavage and Reductive Amination Strategies". Synthesis2004 (11): 1755–1758. 2004. doi:10.1055/s-2004-829135.
↑"Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation". Journal of Medicinal Chemistry48 (10): 3474–3477. May 2005. doi:10.1021/jm050069n. PMID15887955.