2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine
CAS Number
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC11H13N
Molar mass159.232 g·mol−1
3D model (JSmol)
  • c13ccccc3C2CC1CNC2
  • InChI=1S/C11H13N/c1-2-4-11-9-5-8(6-12-7-9)10(11)3-1/h1-4,8-9,12H,5-7H2 checkY
  • Key:COMHUAMOJSTCMM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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, 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

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
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