A-366,833

A-366,833 is a drug developed by Abbott, which acts as an agonist at neural nicotinic acetylcholine receptors selective for the α4β2 subtype, and has been researched for use as an analgesic, although it has not passed clinical trials.[2] Its structure has a nicotinonitrile (3-cyanopyridine) core bound through C5 to the N6 of (1R,5S)-3,6-diazabicyclo[3.2.0]heptane.[3]

A-366,833
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC11H12N4
Molar mass200.239 g·mol−1
3D model (JSmol)
Melting point101.4–102.9 °C (214.5–217.2 °F) [1]
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References
  1. Ji, Jianguo; Schrimpf, Michael R.; Sippy, Kevin B.; Bunnelle, William H.; Li, Tao; Anderson, David J.; Faltynek, Connie; Surowy, Carol S.; Dyhring, Tino; Ahring, Philip K.; Meyer, Michael D. (2007). "Synthesis and Structure−Activity Relationship Studies of 3,6-Diazabicyclo[3.2.0]heptanes as Novel α4β2 Nicotinic Acetylcholine Receptor Selective Agonists". Journal of Medicinal Chemistry. 50 (22): 5493–5508. doi:10.1021/jm070755h. PMID 17929796.
  2. Romanelli, M. Novella; Gratteri, Paola; Guandalini, Luca; Martini, Elisabetta; Bonaccini, Claudia; Gualtieri, Fulvio (2007). "Central nicotinic receptors: structure, function, ligands, and therapeutic potential". ChemMedChem. 2 (6): 746–767. doi:10.1002/cmdc.200600207. PMID 17295372.
  3. Ji, Jianguo; Bunnelle, William H.; Anderson, David J.; Faltynek, Connie; Dyhring, Tino; Ahring, Philip K.; Rueter, Lynne E.; Curzon, Peter; Buckley, Michael J.; Marsh, Kennan C.; Kempf-Grote, Anita; Meyer, Michael D. (2007). "A-366833: A novel nicotinonitrile-substituted 3,6-diazabicyclo[3.2.0]-heptane α4β2 nicotinic acetylcholine receptor selective agonist: Synthesis, analgesic efficacy and tolerability profile in animal models". Biochemical Pharmacology. 74 (8): 1253–1262. doi:10.1016/j.bcp.2007.08.010. PMID 17854775.
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