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Chemical compound
2,3,4,5-tetrahydro-1,5-methano-1H -3-benzazepine
Legal status
2,3,4,5-tetrahydro-1,5-methano-1H -3-benzazepine
CAS Number
ChemSpider
UNII
ChEMBL
Formula C 11 H 13 N
Molar mass 159.232 g·mol−1 3D model (
JSmol )
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
Y Key:COMHUAMOJSTCMM-UHFFFAOYSA-N
Y
N Y
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(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 ,[
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
References
^ 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 .
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