3-Bromocytisine

3-Bromocytisine
Identifiers
	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;
CAS Number	207390-14-5;
PubChem CID	15519735;
ChemSpider	21376088;
Chemical and physical data
Formula	C11H13BrN2O
Molar mass	269.142 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1cc2n(c(=O)c1Br)C[C@H]3C[C@@H]2CNC3;
	InChI 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

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.
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.
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.
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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[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.