3-Bromocytisine

3-Bromocytisine
Systematic (IUPAC) name
(1R,5S)-9-Bromo-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
Clinical data
Identifiers
207390-14-5
PubChem CID 15519735
Chemical data
Formula C11H13BrN2O
269.14 g/mol

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, M. T.; Seitz, G.; Gündisch, D. (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): 375–388. doi:10.1016/S0223-5234(01)01222-3. PMID 11461763.
  2. ↑ Houlihan, L. M.; Slater, Y.; Guerra, D. L.; Peng, J. H.; Kuo, Y. P.; Lukas, R. J.; Cassels, B. K.; Bermudez, I. (2001). "Activity of cytisine and its brominated isosteres on recombinant human alpha7, alpha4beta2 and alpha4beta4 nicotinic acetylcholine receptors". Journal of neurochemistry 78 (5): 1029–1043. doi:10.1046/j.1471-4159.2001.00481.x. PMID 11553677.
  3. ↑ Abin-Carriquiry, J. A. S.; Voutilainen, M. H.; Barik, J.; Cassels, B. K.; Iturriaga-Vásquez, P.; Bermudez, I.; Durand, C.; Dajas, F.; Wonnacott, S. (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, J. A. S.; Urbanavicius, J.; Scorza, C.; Rebolledo-Fuentes, M.; Wonnacott, S.; Cassels, B. K.; Dajas, F. (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.