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]
 | |
| Legal status | |
|---|---|
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C11H13N |
| Molar mass | 159.232 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
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.
See also
editReferences
edit- ^ Mazzocchi PH, Stahly BC (April 1979). "Synthesis and pharmacological activity of 2,3,4,5,-tetrahydro-1,5-methano-1H-3-benzazepines". Journal of Medicinal Chemistry. 22 (4): 455–457. doi:10.1021/jm00190a020. PMID 430484.
- ^ Brooks PR, Caron S, Coe JW, Ng KK, Singer RA, Vazquez E, et al. (2004). "Synthesis of 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine via Oxidative Cleavage and Reductive Amination Strategies". Synthesis. 2004 (11): 1755–1758. doi:10.1055/s-2004-829135.
- ^ Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, et al. (May 2005). "Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation". Journal of Medicinal Chemistry. 48 (10): 3474–3477. doi:10.1021/jm050069n. PMID 15887955.