Epiquinamide: A Poison That Wasn’t from a Frog That Was was written by Fitch, Richard W.;Sturgeon, Gordon D.;Patel, Shaun R.;Spande, Thomas F.;Garraffo, H. Martin;Daly, John W.;Blaauw, Richard H.. And the article was included in Journal of Natural Products in 2009.Name: 1-Chloro-4-iodobutane This article mentions the following:
In 2003, we reported the isolation, structure elucidation, and pharmacol. of epiquinamide (1), a novel alkaloid isolated from an Ecuadoran poison frog, Epipedobates tricolor. Since then, several groups, including ours, have undertaken synthetic efforts to produce this compound, which appeared initially to be a novel, β2-selective nicotinic acetylcholine receptor agonist. Based on prior chiral GC anal. of synthetic and natural samples, the absolute structure of this alkaloid was established as (1S,9aS)-1-acetamidoquinolizidine. We have synthesized the (1R*,9aS*)-isomer (epi-epiquinamide) using an iminium ion nitroaldol reaction as the key step. We have also synthesized ent-1 semisynthetically from (-)-lupinine. Synthetic epiquinamide is inactive at nicotinic receptors, in accord with recently published reports. We have determined that the activity initially reported is due to cross-contamination from co-occurring epibatidine in the isolated material. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Name: 1-Chloro-4-iodobutane).
1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Name: 1-Chloro-4-iodobutane
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com