The general structure of tryptamines.<unk>  is a tryptamine. It has two separate chiral centers, meaning that there are four different stereoisomers of<unk> . These four isomers are difficult to resolve. Synthesis One recent total synthesis of<unk>  and related drugs starts with 2-iodo-4-methoxyaniline which is reacted with triethyl((4-(triethylsilyl)but-3-yn-1-yl)oxy)silane using palladium acetate in DMF to form 2-(triethylsilyl)-3-(2-((triethylsilyl)oxy)ethyl)-1H-indole. This is converted using N-iodosuccinamide and then fluoride to form 2-(2-iodo-1H-indol-3-yl)ethanol. This is treated with iodine, triphenyl phosphine, and imidazole to form 2-iodo-3-(2-iodoethyl)-1H-indole. Then, using 7-ethyl-2-azabicyclo2.2.2oct-5-ene and cesium carbonate in acetonitrile, the<unk>  precursor 7-ethyl-2-(2-(2-iodo-1H-indol-3-yl)ethyl)-2-azabicyclo2.2.2oct-5-ene is obtained. Using palladium acetate in DMF, the<unk>  is obtained. If the exo ethyl group on the 2-azabicyclo2.2.2octane system in<unk>  is replaced with an endo ethyl, then epiibogaine is formed. Crystalline<unk>  hydrochloride is typically produced by semi-synthesis from voacangine in commercial laboratories. It can be prepared from voacangine through one-step demethoxycarbonylation process too. Derivatives A synthetic derivative of<unk> , 18-methoxycoronaridine (18-MC), is a selective α3β4 antagonist that was developed collaboratively by the neurologist Stanley D. Glick (Albany) and the chemist Martin E. Kuehne (Vermont). This discovery was stimulated by earlier studies on other naturally occurring analogues of<unk>  such as coronaridine and voacangine that showed these compounds also have anti-addictive properties. More recently, non- and less- hallucinogenic analogs, tabernanthalog and<unk> log, were engineered by scientists attempting to produce non-cardiotoxic<unk>  derivatives by removing the lipophilic isoquinuclidine ring. In animal models, both molecules failed to produce cardiac arrhythmias and tabernanthalog failed to produce any head twitch response, suggesting psychedelic effects were absent.
Ibogaine
Noribogaine
Oxybuprocaine
Procaine
Levobupivacaine
Tetracaine
Iontocaine
Proxymetacaine