3-Bromocytisine
Identifiers
  • (1R,5S)-9-Bromo-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC11H13BrN2O
Molar mass269.142 g·mol−1
3D model (JSmol)
  • c1cc2n(c(=O)c1Br)C[C@H]3C[C@@H]2CNC3
  • InChI=1S/C11H13BrN2O/c12-9-1-2-10-8-3-7(4-13-5-8)6-14(10)11(9)15/h1-2,7-8,13H,3-6H2/t7-,8+/m0/s1
  • Key:DWDCLEHDNICBMI-JGVFFNPUSA-N

3-Bromocytisine is a derivative of the toxic alkaloid cytisine that acts as a highly potent agonist at neural nicotinic acetylcholine receptors, binding primarily to the α4β2 and α7 subtypes. 3-Bromocytisine is a full agonist at the α7 subtype while it is only a partial agonist at α4β2, but has an extremely strong binding affinity at α4β2 with 200-fold selectivity for α4β2 over α7. In animal studies 3-bromocytisine stimulates the release of dopamine and noradrenaline and increases locomotor activity.[1][2][3][4]

References

  1. ↑ Imming P, Klaperski P, Stubbs MT, Seitz G, Gündisch D (April 2001). "Syntheses and evaluation of halogenated cytisine derivatives and of bioisosteric thiocytisine as potent and selective nAChR ligands". European Journal of Medicinal Chemistry. 36 (4): 375–88. doi:10.1016/S0223-5234(01)01222-3. PMID 11461763.
  2. ↑ Houlihan LM, Slater Y, Guerra DL, Peng JH, Kuo YP, Lukas RJ, et al. (September 2001). "Activity of cytisine and its brominated isosteres on recombinant human alpha7, alpha4beta2 and alpha4beta4 nicotinic acetylcholine receptors". Journal of Neurochemistry. 78 (5): 1029–43. doi:10.1046/j.1471-4159.2001.00481.x. PMID 11553677.
  3. ↑ Abin-Carriquiry JA, Voutilainen MH, Barik J, Cassels BK, Iturriaga-Vásquez P, Bermudez I, et al. (April 2006). "C3-halogenation of cytisine generates potent and efficacious nicotinic receptor agonists". European Journal of Pharmacology. 536 (1–2): 1–11. doi:10.1016/j.ejphar.2006.02.012. PMID 16563372.
  4. ↑ Abin-Carriquiry JA, Urbanavicius J, Scorza C, Rebolledo-Fuentes M, Wonnacott S, Cassels BK, Dajas F (May 2010). "Increase in locomotor activity after acute administration of the nicotinic receptor agonist 3-bromocytisine in rats". European Journal of Pharmacology. 634 (1–3): 89–94. doi:10.1016/j.ejphar.2010.02.030. PMID 20184877.
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