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

2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine;
CAS Number	230615-52-8 ;
ChemSpider	8373558 ;
UNII	5F3AKZ2PNU;
ChEMBL	ChEMBL192387 ;
Chemical and physical data
Formula	C11H13N
Molar mass	159.232 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c13ccccc3C2CC1CNC2;
	InChI 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 ; Key:COMHUAMOJSTCMM-UHFFFAOYSA-N ;
	(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,^{[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.

References[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.

[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.

[pmid15887955-3] 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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