2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine

Chemical compound changed 477209994 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine 1,5-Methano-3-benzazepane.svg 200 Uncontrolled correct CAS 230615-52-8 correct FDA 5F3AKZ2PNU correct EBI 192387 correct chemspider 8373558 11 13 1 c13ccccc3C2CC1CNC2 correct chemspider 1S/C11H13N/c1-2-4-11-9-5-8(6-12-7-9)10(11)3-1/h1-4,8-9,12H,5-7H2 correct chemspider COMHUAMOJSTCMM-UHFFFAOYSA-N 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. Mazzocchi PH, Stahly BC Synthesis and pharmacological activity of 2,3,4,5,-tetrahydro-1,5-methano-1H-3-benzazepines Journal of Medicinal Chemistry 22 4 455–457 April 1979 430484 10.1021/jm00190a020 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. Brooks PR, Caron S, Coe JW, Ng KK, Singer RA, Vazquez E, Vetelino MG, Watson HH, Whritenour DC, Wirtz MC 6 Synthesis of 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine via Oxidative Cleavage and Reductive Amination Strategies 10.1055/s-2004-829135 Synthesis 2004 11 1755–1758 2004 Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, Sands SB, Davis TI, Lebel LA, Fox CB, Shrikhande A, Heym JH, Schaeffer E, Rollema H, Lu Y, Mansbach RS, Chambers LK, Rovetti CC, Schulz DW, Tingley FD, O'Neill BT 6 Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation Journal of Medicinal Chemistry 48 10 3474–3477 May 2005 15887955 10.1021/jm050069n More recently this chemical compound is claimed to have been sold as a designer drug under the name A3A,February 2011 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. See also Corey lactone 4-phenylbenzoate References 2 Category:Nicotinic agonists Category:Benzazepines Category:Stimulants