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
  • 5-[(1R,5S)-3,6-Diazabicyclo[3.2.0]hept-6-yl]pyridine-3-carbonitrile
CAS Number
PubChem CID
ChemSpider
UNII
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]
  • N#CC1=CN=CC(N2[C@]3([H])CNC[C@]3([H])C2)=C1
  • InChI=1S/C11H12N4/c12-2-8-1-10(5-13-3-8)15-7-9-4-14-6-11(9)15/h1,3,5,9,11,14H,4,6-7H2/t9-,11-/m1/s1 ☒N
  • Key:GPXAWLDGWSBLKM-MWLCHTKSSA-N ☒N
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References
  1. Ji J, Schrimpf MR, Sippy KB, Bunnelle WH, Li T, Anderson DJ, et al. (November 2007). "Synthesis and structure-activity relationship studies of 3,6-diazabicyclo[3.2.0]heptanes as novel alpha4beta2 nicotinic acetylcholine receptor selective agonists". Journal of Medicinal Chemistry. 50 (22): 5493–508. doi:10.1021/jm070755h. PMID 17929796.
  2. Romanelli MN, Gratteri P, Guandalini L, Martini E, Bonaccini C, Gualtieri F (June 2007). "Central nicotinic receptors: structure, function, ligands, and therapeutic potential". ChemMedChem. 2 (6): 746–67. doi:10.1002/cmdc.200600207. PMID 17295372. S2CID 34763474.
  3. Ji J, Bunnelle WH, Anderson DJ, Faltynek C, Dyhring T, Ahring PK, et al. (October 2007). "A-366833: a novel nicotinonitrile-substituted 3,6-diazabicyclo[3.2.0]-heptane alpha4beta2 nicotinic acetylcholine receptor selective agonist: Synthesis, analgesic efficacy and tolerability profile in animal models". Biochemical Pharmacology. 74 (8): 1253–62. doi:10.1016/j.bcp.2007.08.010. PMID 17854775.
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